Category: 33786-89-9

Related Products of 33786-89-9,Some common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, molecular formula is C6H7ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

STR4 Using the above description one ordinarily skilled in the art can make and use the compounds of this invention. Specific embodiments of the invention are provided below. Structures and names of the embodied compounds are found summarized in CHART C. The examples below serve to illustrate the invention and are not intended to limit the invention in any manner. Example 1. Synthesis of N-(3-azido-5-ehlorophenyl)-N’-cyano-N”-(1,1dimethylpropyl)guanidine. Chart A. Step A-2. A stirred solution of 5-chloro-1,3-phenylenediamine (A-1, X is Cl, 1.93 g, 13.5 mmol) in 55 mL of dichloromethane is cooled to 0 C. and di-tert-butyl dicarbonate (2.96 g, 13.5 mmol) is added. The reaction mixture is stirred at 20-25 C. for 5 days and then concentrated. The residue is purified by medium pressure liquid chromatography using 25% ethyl acetate in hexane to afford 2.20 g of 3-amino-5-chlorophenylcarbamic acid, 1,1-dimethylethyl ester. (A-2) mp 85-87 C.; IR (mull) 3439, 3357, 3328, 2926, 1691, 1613, 1589, 1524, 1475, 1438, 1391, 1366, 1311, 1274, 1240, 1159, 851 cm-1; 1 H NMR (CDCl3) delta6.77 (bs, 1 H), 6.64 (m, 1 H), 6.39 (bs, 1 H), 6.34 (m, 1 H), 3.73 (bs, 2 H), 1.50 (s, 9 H); 13 C NMR (CDCl3) delta152.1, 147.8, 139.9, 134.8, 109.4, 108.2, 102.6, 80.5, 28.2; Analysis calculated for C11 H15 CIN2 O2: C, 54.44; H, 6.23; N, 11.54; Cl, 14.61. Found: C, 54.27; H, 6.50; N, 10.96; Cl, 13.99.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-m-phenylenediamine, its application will become more common.

Reference:
Patent; The Upjohn Company; US5525742; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 33786-89-9,Some common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, molecular formula is C6H7ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[3]: 1.1-(4-Methoxyphenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (500 mg, 1.75 mmol, 1 equiv) was dissolved in .5 mL dry DMF under inert atmosphere with HATU (732 mg, 1.93 mmol, 1.1 equiv). While stirring, DIPEA (1.8 g, 14 mmol, 8 equiv) was added drop wise at 0 C. When all the DIPEA was added, it was allowed to sit for 15 minutes. After this, 5-chloro-m-phenylenediamine (996 mg, 7.0 mmol, 4 equiv) was added. The reaction was allowed to warm up to R.T. over the course of 2 hrs and was monitored by TLC and LC/MS. When complete, 5 mL of H2O and 5 mL of EtOAc were added and the mixture transferred to a seperatory funnel. The aqueous layer was extracted into EtOAc (5 mL X 3). The crude product was dissolved in 1 : 1 ACN : H2O, separated by RP-HPLC (H2O [.1% TFA] : ACN [.1% TFA]), and lyophilized to afford the coupled intermediate as a clear oil (410.78 g/mol, 245 mg, 34% yield).2. A portion of the purified product from step one (100 mg, .22 mmol, 1 equiv) was dissolved in .5 mL dry DMF under inert atmosphere. Dry TEA (90 mg, .85 mmole, 4 equiv) was added via syringe at 0 C.20 mL of acryloyl chloride was transferred via syringe to the reaction vial (22 mg, .242 mmol, 1.1 equiv) at 0 C. The reaction was allowed to warm up to R. T. and was monitored by TLC and LC/MS. Once complete, 1 mL of saturated NaHCO3 solution was added and allowed to mix for 15 minutes to quench the reaction. To this, 5 mL of EtOAc was added and the mixture was transferred to a seperatory funnel. The aqueous layer was extracted into EtOAc (5 mL X 3). The crude product was dissolved in 1 : 1 ACN : H2O, separated by RP-HPLC (H2O [.1% TFA] : ACN [.1% TFA]), and lyophilized to afford compound 3 as a clear oil (464.78 g/mol, 48 mg, 47% yield).1H (500 MHz, (CD3)2SO) d: 10.71 (s, 1H), 10.41 (s, 1H), 8.05 (m, 1H), 7.69 (m, 1H), 7.49 (m, 1H), 8.29 (s, 1H), 7.46 (m, 2H), 7.12 (m, 2H), 6.44(dd, J1 = 17.00Hz, J2= 10.08 Hz, 1H), 6.30(dd, J1 = 17.00 Hz, J2= 1.76Hz, 1H), 5.80(dd, J1 = 10.08 Hz, J2= 1.76Hz, 1H), 3.85(s, 3H).13C (125 MHz, (CD3)2SO) d: 163.47, 160.15, 159.32, 140.64, 140.25, 139.55, 133.08, 131.51, 131.46, 127.64, 127.47 (2C), 120.74, 120.38, 118.22, 114.40 (2C), 114.28, 114.26, 108.83, 55.60.; [4]: 1. Please refer to step one of the synthesis of compound 3 above.2. A portion of the purified coupled intermediate from step one compound 3?s synthesis (100 mg, .22 mmol, 1 equiv) was dissolved in .5 mL dry DMF under inert atmosphere. Dry TEA (90 mg, .85 mmole, 4 equiv) was added via syringe at 00C.20 mL of propionyl chloride was transferred via syringe to the reaction vial (22 mg, .242 mmol, 1.1 equiv) at 00C. The reaction was allowed to warm up to R. T. and was monitored by TLC and LC/MS. Once complete, 1 mL of saturated NaHCO3 solution was added and allowed to mix for 15 minutes to quench the reaction. To this, 5 mL of EtOAc was added and the mixture was transferred to a seperatory funnel. The aqueous layer was extracted into EtOAc (5 mL X 3). The crude product was dissolved in 1 : 1 ACN : H2O, separated by RP-HPLC (H2O [.1% TFA] : ACN [.1% TFA]), and lyophilized to afford compound 4 as a clear oil (466.8 g/mol, 74 mg, 72% yield).1H (500 MHz, (CD3)2SO) d: 10.66 (s, 1H), 10.12 (s, 1H), 8.28, (s, 1H), 7.97 (m, 1H), 7.58 (m, 1H), 7.46 (m, 3H), 7.12 (m, 2H), 3.85 (s, 3H), 2.33 (q, J = 7.6 Hz, 2H), 1.08 (t, J = 7.6 Hz, 3H).13C (125 MHz, (CD3)2SO) d: 172.47, 160.13, 159.29, 140.96, 140.16, 139.54, 132.96, 131.47, 127.47 (2C), 120.78, 120.39, 118.22, 114.40 (2C), 113.97, 113.73, 108.52, 55.60, 29.56, 9.53.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-m-phenylenediamine, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SHOKAT, Kevan, M.; GENTILE, Daniel; MOSS, Steven; (380 pag.)WO2018/112420; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 33786-89-9, These common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 22 (3-Azido-5-chlorophenyl)-(6,7-dimethoxyquinazolin-4-yl)amine 4-Chloro-6,7-dimethoxyquinazoline (200 mg, 0.89 mmol) and 5-amino-3-chloroaniline (253 mg, 1.78 mmol) were combined in isopropanol (3 mL) and heated to reflux for 16 hours under an atmosphere of dry nitrogen. After cooling to 20C the mixture was diluted with methanol (5 mL) and the resulting precipitate was filtered and dried, in vacuo, to afford 252 mg (77%) of (3-amino-5-chlorophenyl)-(6,7-dimethoxyquinazolin-4-yl)amine hydrochloride (mp. 298-301C; LC-MS: 331 (MH+)).

Statistics shows that 5-Chloro-m-phenylenediamine is playing an increasingly important role. we look forward to future research findings about 33786-89-9.

Reference:
Patent; PFIZER INC.; EP1110953; (2001); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33786-89-9, name is 5-Chloro-m-phenylenediamine, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

A suspension of 2,6-dichloro-9-isopropyl-9H-purine (3.0 g, 12 mmol) and 5-chlorobenzene-1,3-diamine (1.8 g, 12 mmol) in n-butanol (21 mL) was stirred at rt as DIPEA (4.1 mL, 24 mmol) was added drop-wise. The resulting suspension was allowed to stir at 100 C and the suspension became a clear solution. After 8 h heating, the solution became a suspension. This suspension was allowed to cool to rt and filtered. The solids were washed with EtOAc (2×10 mL) and dried under vacuum. The title compound (3.6 g) was recovered as solid in 83% yield. 1H NMR (399 MHz, DMSO-d6) delta 10.08 (s, 1H), 8.42 (s, 1H), 7.10 (t, J = 1.9 Hz, 1H), 6.96 (t, J = 1.9 Hz, 1H), 6.33 (t, J = 2.0 Hz, 1H), 5.41 (s, 2H), 4.71 (p, J = 6.8 Hz, 1H), 1.51 (d, J = 6.7 Hz, 6H); 13C NMR (75 MHz, DMSO-d6) delta 152.7, 152.3, 150.7, 150.6, 141.0, 140.9, 133.4, 119.6, 109.2, 108.9, 105.4, 47.4, 22.6, 22.5; HRMS (ESI) m/z calcd for C14H14Cl2N6 (M + H)+, 337.0730; found, 337.0727.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 33786-89-9.

Reference:
Article; Shi, Yihui; Park, Jaehyeon; Lagisetti, Chandraiah; Zhou, Wei; Sambucetti, Lidia C.; Webb, Thomas R.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 406 – 412;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 33786-89-9, name is 5-Chloro-m-phenylenediamine, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 33786-89-9, Formula: C6H7ClN2

4-Chloro-6,7-dimethoxyquinazoline (200 mg, 0.89 mmol) and 5-amino-3-chloroaniline (253 mg, 1.78 mmol)were combined in isopropanol (3 mL) and heated to reflux for 16 hours under an atmosphere of dry nitrogen. After coolingto 20C the mixture was diluted with methanol (5 mL) and the resulting precipitate was filtered and dried, in vacuo, toafford 252 mg (77%) of (3-amino-5-chlorophenyl)-(6,7-dimethoxyquinazolin-4-yl)amine hydrochloride (mp. 298-301 C;LC-MS: 331 (MH+)). A portion of this product (175 mg, 0.476 mmol) was dissolved in 80% acetic acid/H2O (12 mL),cooled to 0C, and a solution of NaNO2 (36 mg, 0.516 mmol) in H2O (300 mL) was added. The solution was stirred for10 minutes at 0C and NaN3 (33 mg, 0.50 mmol) in H2O (300 mL) was added. The reaction mixture was allowed to warmto 20C and stirred 16 hours. The resulting precipitate was filtered and dissolved in 10% methanol in CHCl3 and thesolution was washed with saturated aqueous NaHCO3, and brine, dried over Na2SO4, filtered and concentrated in vacuoto yield 59 mg (35%) of the title product as a yellow solid; mp 205-206C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-m-phenylenediamine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Products Inc.; OSI Pharmaceuticals, LLC; Schnur, Rodney Caughren; Arnold, Lee Daniel; (28 pag.)EP2163546; (2016); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 33786-89-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 33786-89-9 as follows.

DMAP (50 mg) and acetic anhydride (3.9 g, 37.9 mmol) were added sequentially and dropwise to a cold solution of 5-chloro-benzene-1 ,3-diamine (4.5 g, 31.6 mmol) in pyridine (22 ml.) keeping the internal temperature below 0C. The reaction mixture was allowed to warm to rt, stirred for 2 h, cooled to 0C, quenched by addition of ice cooled water, and extracted with EtOAc. The organic phase was washed with brine, dried (Na2S04), filtered, and concentrated. The crude material was purified by silica gel column chromatography (CH2CI2/MeOH, 99: 1 ) to afford the title compound. tR: 0.18 min (LC-MS 2); ESI-MS: 184.9 [M+H]+(LC-MS 2); Rf= 0.32 (hexane/EtOAc, 1 :4).

According to the analysis of related databases, 33786-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; MAH, Robert; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/80141; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33786-89-9,Some common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, molecular formula is C6H7ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

STR4 Using the above description one ordinarily skilled in the art can make and use the compounds of this invention. Specific embodiments of the invention are provided below. Structures and names of the embodied compounds are found summarized in CHART C. The examples below serve to illustrate the invention and are not intended to limit the invention in any manner. Example 1. Synthesis of N-(3-azido-5-ehlorophenyl)-N’-cyano-N”-(1,1dimethylpropyl)guanidine. Chart A. Step A-2. A stirred solution of 5-chloro-1,3-phenylenediamine (A-1, X is Cl, 1.93 g, 13.5 mmol) in 55 mL of dichloromethane is cooled to 0 C. and di-tert-butyl dicarbonate (2.96 g, 13.5 mmol) is added. The reaction mixture is stirred at 20-25 C. for 5 days and then concentrated. The residue is purified by medium pressure liquid chromatography using 25% ethyl acetate in hexane to afford 2.20 g of 3-amino-5-chlorophenylcarbamic acid, 1,1-dimethylethyl ester. (A-2) mp 85-87 C.; IR (mull) 3439, 3357, 3328, 2926, 1691, 1613, 1589, 1524, 1475, 1438, 1391, 1366, 1311, 1274, 1240, 1159, 851 cm-1; 1 H NMR (CDCl3) delta6.77 (bs, 1 H), 6.64 (m, 1 H), 6.39 (bs, 1 H), 6.34 (m, 1 H), 3.73 (bs, 2 H), 1.50 (s, 9 H); 13 C NMR (CDCl3) delta152.1, 147.8, 139.9, 134.8, 109.4, 108.2, 102.6, 80.5, 28.2; Analysis calculated for C11 H15 CIN2 O2: C, 54.44; H, 6.23; N, 11.54; Cl, 14.61. Found: C, 54.27; H, 6.50; N, 10.96; Cl, 13.99.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-m-phenylenediamine, its application will become more common.

Reference:
Patent; The Upjohn Company; US5525742; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 33786-89-9,Some common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, molecular formula is C6H7ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[3]: 1.1-(4-Methoxyphenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (500 mg, 1.75 mmol, 1 equiv) was dissolved in .5 mL dry DMF under inert atmosphere with HATU (732 mg, 1.93 mmol, 1.1 equiv). While stirring, DIPEA (1.8 g, 14 mmol, 8 equiv) was added drop wise at 0 C. When all the DIPEA was added, it was allowed to sit for 15 minutes. After this, 5-chloro-m-phenylenediamine (996 mg, 7.0 mmol, 4 equiv) was added. The reaction was allowed to warm up to R.T. over the course of 2 hrs and was monitored by TLC and LC/MS. When complete, 5 mL of H2O and 5 mL of EtOAc were added and the mixture transferred to a seperatory funnel. The aqueous layer was extracted into EtOAc (5 mL X 3). The crude product was dissolved in 1 : 1 ACN : H2O, separated by RP-HPLC (H2O [.1% TFA] : ACN [.1% TFA]), and lyophilized to afford the coupled intermediate as a clear oil (410.78 g/mol, 245 mg, 34% yield).2. A portion of the purified product from step one (100 mg, .22 mmol, 1 equiv) was dissolved in .5 mL dry DMF under inert atmosphere. Dry TEA (90 mg, .85 mmole, 4 equiv) was added via syringe at 0 C.20 mL of acryloyl chloride was transferred via syringe to the reaction vial (22 mg, .242 mmol, 1.1 equiv) at 0 C. The reaction was allowed to warm up to R. T. and was monitored by TLC and LC/MS. Once complete, 1 mL of saturated NaHCO3 solution was added and allowed to mix for 15 minutes to quench the reaction. To this, 5 mL of EtOAc was added and the mixture was transferred to a seperatory funnel. The aqueous layer was extracted into EtOAc (5 mL X 3). The crude product was dissolved in 1 : 1 ACN : H2O, separated by RP-HPLC (H2O [.1% TFA] : ACN [.1% TFA]), and lyophilized to afford compound 3 as a clear oil (464.78 g/mol, 48 mg, 47% yield).1H (500 MHz, (CD3)2SO) d: 10.71 (s, 1H), 10.41 (s, 1H), 8.05 (m, 1H), 7.69 (m, 1H), 7.49 (m, 1H), 8.29 (s, 1H), 7.46 (m, 2H), 7.12 (m, 2H), 6.44(dd, J1 = 17.00Hz, J2= 10.08 Hz, 1H), 6.30(dd, J1 = 17.00 Hz, J2= 1.76Hz, 1H), 5.80(dd, J1 = 10.08 Hz, J2= 1.76Hz, 1H), 3.85(s, 3H).13C (125 MHz, (CD3)2SO) d: 163.47, 160.15, 159.32, 140.64, 140.25, 139.55, 133.08, 131.51, 131.46, 127.64, 127.47 (2C), 120.74, 120.38, 118.22, 114.40 (2C), 114.28, 114.26, 108.83, 55.60.; [4]: 1. Please refer to step one of the synthesis of compound 3 above.2. A portion of the purified coupled intermediate from step one compound 3?s synthesis (100 mg, .22 mmol, 1 equiv) was dissolved in .5 mL dry DMF under inert atmosphere. Dry TEA (90 mg, .85 mmole, 4 equiv) was added via syringe at 00C.20 mL of propionyl chloride was transferred via syringe to the reaction vial (22 mg, .242 mmol, 1.1 equiv) at 00C. The reaction was allowed to warm up to R. T. and was monitored by TLC and LC/MS. Once complete, 1 mL of saturated NaHCO3 solution was added and allowed to mix for 15 minutes to quench the reaction. To this, 5 mL of EtOAc was added and the mixture was transferred to a seperatory funnel. The aqueous layer was extracted into EtOAc (5 mL X 3). The crude product was dissolved in 1 : 1 ACN : H2O, separated by RP-HPLC (H2O [.1% TFA] : ACN [.1% TFA]), and lyophilized to afford compound 4 as a clear oil (466.8 g/mol, 74 mg, 72% yield).1H (500 MHz, (CD3)2SO) d: 10.66 (s, 1H), 10.12 (s, 1H), 8.28, (s, 1H), 7.97 (m, 1H), 7.58 (m, 1H), 7.46 (m, 3H), 7.12 (m, 2H), 3.85 (s, 3H), 2.33 (q, J = 7.6 Hz, 2H), 1.08 (t, J = 7.6 Hz, 3H).13C (125 MHz, (CD3)2SO) d: 172.47, 160.13, 159.29, 140.96, 140.16, 139.54, 132.96, 131.47, 127.47 (2C), 120.78, 120.39, 118.22, 114.40 (2C), 113.97, 113.73, 108.52, 55.60, 29.56, 9.53.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-m-phenylenediamine, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SHOKAT, Kevan, M.; GENTILE, Daniel; MOSS, Steven; (380 pag.)WO2018/112420; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 33786-89-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 33786-89-9, name is 5-Chloro-m-phenylenediamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-chloro-1,3-phenylenediamine (15.0 g, 0.105 mol) in 70 mL ethanol was added ethyl 4,4,4-trifluoroacetoacetate (20.4 g, 0.111 mol), then the mixture was heated at reflux for 18 h. The solvent was removed under reduced pressure until the product began to precipitate. The material was allowed to crystallize for 2 h, whereupon it was filtered and rinsed with cold ether to afford 10.9 g (37%) of 5-amino-7-chloro-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one, a tan solid. The filtrate was concentrated until solid began to precipitate and afforded an additional 3.0 g (10%). 1H NMR (400 MHz, acetone-d6) delta11.0 (broad s, 1H), 9.64 (s, 1H), 7.42 (t, 1H, J=8.1), 6.99 (d, 1H, J=8.1), 6.90 (s, 1H), 6.79 (d, 1H, J=8.1).

The synthetic route of 5-Chloro-m-phenylenediamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US2002/183314; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33786-89-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33786-89-9, name is 5-Chloro-m-phenylenediamine, This compound has unique chemical properties. The synthetic route is as follows.

REFERENCE EXAMPLE 75 To a solution of 5-chloro-1,3-benzenediamine (7.48 g) in tetrahydrofuran (50 ml) was added slowly a 1.5M solution of n-butyl lithium in n-hexane (27.3 ml) at 0 C. The resultant mixture was stirred for 30 minutes at 0 C. To the mixture was added a solution of 3-chloro-6-fluorobenzo[d]isoxazole (1.8 g) in tetrahydrofuran (5 ml). After stirring for 15 minutes at 0 C. and for an hour at ambient temperature, the reaction mixture was poured into a mixture of water and ethyl acetate. The separated organic layer was washed well with 1N-hydrochloric acid and dried over potassium carbonate. After evaporation under reduced pressure, the residue was crystallized from methanol to give 5-chloro-N-(6-fluorobenzo[d]isoxazol-3-yl)benzene-1,3-diamine (1.54 g). APCI-Mass: 278 (m/z, (M+H)+) NMR(DMSO-d6, delta): 5.50(2H, s), 6.24(1H, t, J=3.7 Hz), 6.88(2H, t, J=1.9 Hz), 7.27(1H, dt, J=2.1, 9.0 Hz), 7.57(1H, dd, J=2.1, 9.0 Hz), 8.09-8.22(1H, m), 9.47(1H, s).

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-m-phenylenediamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamada, Akira; Spears, Glen; Hayashida, Hisashi; Tomishima, Masaki; Ito, Kiyotaka; Imanishi, Masashi; US2003/176454; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics