Author: tianli

Adding a certain compound to certain chemical reactions, such as: 95-51-2, name is 2-Chloroaniline, 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 95-51-2, 95-51-2

General procedure: Into a pressure microreactor of stainless steel of 17 mL capacity or into a glass ampule (20 mL) (results of the parallel runs were virtually identic) was charged 5-10 wt % of catalyst (0.94HY-BS, NaY-BS, 0.72KNaX-BS), 100 mmol of aniline or its derivative, and 400 mmol of dimethyl carbonate. The reactor was hermetically closed (the ampule was sealed), and was heated for 1-4 h at 150 C. After the end of the run the reactor was cooled to room temperature, opened, the reaction mixture was filtered through a bed of Al2O3. Dimethyl carbonate was distilled off, the residue was distilled at atmospheric pressure or in a vacuum, or crystallized from ethanol.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Khusnutdinov; Shchadneva; Mayakova, Yu. Yu.; Ardieva; Khazipova; Kutepov; Russian Journal of Organic Chemistry; vol. 52; 11; (2016); p. 1565 – 1570; Zh. Org. Khim.; vol. 52; 11; (2016); p. 1574 – 1578,5;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, molecular formula is C8H9ClO, 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. 54788-38-4

Intermediate 49a: 1-Bromomethyl-2-chloro-4-methoxy-benzene BR A suspension of 3-chloro-4-methylanisole (2.23 g, 14. 24 mmol), N-bromosuccinimide (2.53 g, 14.24 MMOL), and 70% benzoyl peroxide (493 mg, 1.424 MMOL) in 40 mL CCI4 was heated to reflux at 80C for two hours. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated under rotary evaporator. The residue was purified by flash column chromatography eluting with 5% EtOAc in Hexane to provide 2.25 g of intermediate 49a as a white SOLID. 1H NMR (300 MHz, CDCl3) 8 7.33 (d, 1H, J = 8.48 HZ), 6.93 (d, 1H, J = 2.63 Hz), 6.81-6. 75 (m, 1 H), 4.58 (m, 2H), 3.79 (m, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-methoxy-1-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; WO2005/21554; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, 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. 1996-29-8

Potassium /-butoxide (3.9 g, 0.33 mmol) was dissolved in DMSO (25 mL). To this solution was added 3 -methyl pyrazole (2.7 g, 0.33 mmol) and the reaction was heated at 50 C for 30 min. l-Bromo-4-chloro-2-fluorobenzene (4.6 g, 0.22 mmol) was then added and the reaction was stirred at 50 C for 16 h. The reaction was cooled to RT and extracted with water and EtOAc, washed with brine, and dried over Na2S04) filtered and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtO Ac/heptane) provided l-(2- bromo-5-chlorophenyl)-3-methyl-lH-pyrazole and l-(2-bromo-5-chloroplienyl)-5-methyl-lH- pyrazole as a 4: 1 mixture that was used in the next step directly,l-(2-biOmo-5-chlorophenyl)-3-methyl-lH-pyrazole/l-(2-bi mo-5-chlorophenyl)-5- methyl-lH-pyrazole mixture (Intermediate 3, step 1) (1 ,00 g, 3.68 mmol) was dissolved in THF (6 mL) then cooled to 0 C, /-Propyl magnesium chloride (2,76 mL, 2.0 M in THF, 5.52 mmol) was added dropwise and the reaction was warmed to RT for 30 min. The reaction was then cooled to -15 C and paraformaldehyde (166 mg, 5.5 mmol) was added. The reaction mixture was allowed to warm to RT and stirred for 1 h. DMF (500 mL) was added and the reaction was stirred for an additional 1 h. The reaction was quenched with HC1 (2 N, 4 mL), diluted with water, extracted with EtOAc, washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtOAc/heptane) provided 4-chloro-2-(3-methyl-pyrazoI-l -yl)-benzaldehyde

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 1996-29-8.

Reference:
Patent; KAROS PHARMACEUTICALS, INC.; DE LOMBAERT, Stephane; GOLDBERG, Daniel R.; BRAMELD, Kenneth; SJOGREN, Eric Brian; SCRIBNER, Andrew; WO2015/35113; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

627-42-9, Adding some certain compound to certain chemical reactions, such as: 627-42-9, name is 2-Methoxyethyl chloride, 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 627-42-9.

Adding 76.1 g (0.5 mol) of methyl salicylate to 250 ml of N-methylpyrrolidone,2-chloromethyl ethyl ether 56.7 g (0.6 mol),Potassium iodide 8.3g (0.05mol),Potassium carbonate 82.9g (0.6mol),It was stirred at 120 C for 16 hours.After cooling the reaction solution, 300 ml of water was added,Extracted with 300 ml of ethyl acetate,After washing the ethyl acetate solution with saturated brine,The solvent was distilled off. Thereafter, 40 g of a 50% aqueous NaOH solution, 40 ml of water, and 40 ml of ethanol were added.It was stirred at 100 C for 1 hour.After the reaction is completed, hydrochloric acid water is added for neutralization.Ethyl acetate was added for extraction.The ethyl acetate solution is washed with saturated brine.The solvent was distilled off. Thereafter,Purification by ruthenium column chromatographyAnd get 59g(yield 60%)Intermediate 4.

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 627-42-9.

Reference:
Patent; Fujifilm Corporation; Takasaki, Yuta; Sasaki, Daisuke; Ishizaka, Soji; (141 pag.)TWI626233; (2018); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

348-59-4, 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 348-59-4 as follows.

Step 1 a) The mixture of 1 ,4-dichloro-2-fluoro-benzene (5.4 g, 0.0327 mol), AICI3 (10.4 g, 0.0784 mol) was warmed to 60 C, and acetyl chloride (3.85 g, 0.0491 mol) was added by syringe over 5 min under N2, the mixture was warmed to 100 C for 2h. Then the mixture was added into ice water and adjusted pH to 2 by 1 N HCI. Extracted by MTBE (100 ml*2), dried and concentrated to give 1 – (2,5-dichloro-4-fluoro-phenyl)ethanone (6g, crude). 1H NMR : CDCI3 400MHz, delta (ppm)= 2.58 (s, 3 H), 7.19 (d, J=8.38 Hz, 1 H), 7.63 (d, J=7.94 Hz, 1 H).

According to the analysis of related databases, 2,5-Dichlorofluorobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; GRAMMENOS, Wassilios; CRAIG, Ian Robert; BOUDET, Nadege; MUeLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica May Wilson; LOHMANN, Jan Klaas; GROTE, Thomas; HADEN, Egon; ESCRIBANO CUESTA, Ana; WO2014/82879; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

26487-67-2, 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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,1-bis(4-hydroxyphenyl)-2-cyclohexyl-2-phenylethene (37.6 mg, 0.101 mmol) in DMF (1.02 mL) at 0 ¡ãC was added 60percent sodium hydride (dispersion in paraffin liquid, 24.4 mg, 0.610 mmol). The reaction mixture was stirred for 15 min at 50 ¡ãC and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (66.4 mg, 0.335 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 15.5 h at 50 ¡ãC, saturated aqueous ammonium chloride was added at 0 ¡ãC. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 9/1) to afford RID-F-S*13 (compound 9) (51.9 mg, 83percent) as a pale yellow oil

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hasegawa, Makoto; Yasuda, Yukari; Tanaka, Makoto; Nakata, Kenya; Umeda, Eri; Wang, Yanwen; Watanabe, Chihiro; Uetake, Shoko; Kunoh, Tatsuki; Shionyu, Masafumi; Sasaki, Ryuzo; Shiina, Isamu; Mizukami, Tamio; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 290 – 305;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6579-54-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6579-54-0 name is 2,6-Dichlorobenzenesulfonyl chloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a mixture of 2,4-dichloro-5-methylpyrimidine (4.17g, 25.6mmol) and 4-acetamidophenylboronic acid (5.Og, 27.9mmol) in DME (40ml) was added Et3N (8.92ml, 64.0mmol), H2O (4ml), and dichloro[l,r-bis(diphenylphosphino)ferrocenepalladium (2.8 Ig, 3.44mmol, 13%). The mixture was allowed to stir at reflux for 5hrs. After the mixture was cooled down to rt, the crude mixture was directly filtered on silica gel and eluted with EtOAc. The filtrate was concentrated in vacuo. Further purification was conducted by flash chromatography to afford Intermediate 1 (5.94g, 89%) as a white solid. LCMS: m/z 262 (M+H)+.[0246] To a stirred solution of chloropyrimidine (1.05g, 4.0mmol) in 1-butanol (10ml) was added N-Boc-amino-3-aniline (920mg, 4.4mmol) and the mixture was heated in the sealed tube at 18O0C for 1.5hr. The mixture was cooled down to rt and acidified with IN HCl (20ml). The aqueous layer was washed with EtOAc (50ml). The separated aqueous layer was basified with 2N NaOH to pH 8-9 and extracted with EtOAc (50ml*3). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by flash 5 chromatography to afford product Intermediate K (943mg, 71% as a light yellow solid. LCMS: m/z 334 (M+H)+.[02471 To a stirred suspension of aniline (250mg, 0.75mmol) in THF (5ml) was added DIPEA (157ml, 0.90mmol) and 2,6-dichlorobenzenesulfonyl chloride (203 mg, 0.83mmol) and the mixture containing intermediate K was stirred at reflux for 2hrs. After cooling down to rt, the mixture was diluted with EtOAc, washed with H?O, brine, and dried over Na2SO4. After concentrated in vacuo, the residue was purified by flash chromatography to give product 26 (299mg, 73%) as a light pink solid.1H-NMR (400MHz, d6-DMSO): 10.71 (s, IH), 10.16 (s, IH), 9.54 (s, IH), 8.34 (s, IH), 7.75- 7.69 (m, 5H), 7.60 (dd, 2H), 7.51 (dd, IH), 7.31 (dd, IH), 7.09 (t, IH), 6.66 (dd, IH), 2.25 (s, 3H), 2.08 (s, 3H); MS (EI) C25H2ICl2N5O3S: 542.2 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorobenzenesulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; WO2007/89768; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 1871-57-4 as follows. 1871-57-4

To sodium hydride (60 wt.% in mineral oil, 2.464 g, 61.6 mmol) in DMF (50 mL) was added 3-chloro-2-(chloromethyl)prop-l-ene (3.5 g, 28.0 mmol) at ~5 C (ice bath) and a solution of tert-butyl(2-hydroxyethyl)carbamate (4.51 g, 28.0 mmol) in tetrahydrofuran (50 mL). The reaction mixture was stirred at 20-30 C for ~2 hrs and concentrated under reduced pressure to remove tetrahydrofuran. The resulting mixture was poured into water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 80 g, EtO Ac/heptane = 0/100 to 50/50] providing tert-butyl 6-methylene-l ,4-oxazepane-4- carboxylate (4 g) as a colorless oil. NMR (400 MHz, chloroform-d) delta [ppm]: 1.46 (s, 9 H) 3.33 – 3.62 (m, 2 H) 3.62 – 3.82 (m, 2 H) 4.09 (m, 2 H) 4.16 (m, 2 H) 4.99 (m,2 H).

According to the analysis of related databases, 1871-57-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; PFISTER, Keith B; SENDZIK, Martin; WO2011/26917; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

933190-51-3, The chemical industry reduces the impact on the environment during synthesis 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life.

A mixture of 8-bromo-6-chloroimidazo[l,2-b]pyridazine (2 g, 8.6 mmol) and 5,6- dimethoxypyridin-2-amine (1.39 g, 9.03 mmol) in DMF (72 ml) was cooled to 0 C. To the mixture was added sodium hydride (1.1 g, 27.5 mmol, 60% dispersion in mineral oil). The reaction was stirred for 10 min then warmed to room temperature. After 15 h the reaction was quenched with saturated sodium bicarbonate solution, and then diluted with water and EtOAc. An insoluble solid was filtered off. The filtrate was separated and the aqueous phase was washed with EtOAc. The combined organic extracts were concentrated in vacuo and the residue obtained was crystalized from methanol to give 6-chloro-N-(5,6-dimethoxypyridin -2- yl)imidazo[l,2-b]pyridazin-8-amine (2.4 g, 7.85 mmo 1, 91.2 %) as light brown needles. 1H NMR (300 MHz, CHLOROFORM- ) delta ppm 8.26 (br. s., 1 H) 7.95 (s, 1 H) 7.81 (s, 1 H) 7.55 (s, 1 H) 7.15 (d, J=7.93 Hz, 1 H) 6.58 (d, J=8.31 Hz, 1 H) 4.12 (s, 3 H) 3.89 (s, 3 H); LC/MS: 305.9 [MH]+.

The chemical industry reduces the impact on the environment during synthesis 8-Bromo-6-chloroimidazo[1,2-b]pyridazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

83121-15-7, Name is 3,5-Dichloro-2,4-difluoroaniline, 83121-15-7, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Example 10 N-(2,4-Difluoro-3,5-dichlorophenyl)-N’-(2,6-difluorobenzoyl)-urea Three grams (0.016 mol) of 2,6-difluoro-benzoyl isocyanate were added to a solution of 2.95 gm (0.015 mol) of 2,4-difluoro-3,5-dichloroaniline in 50 ml of toluene. The solution thus obtained was stirred for 15 hours at room temperature. Thereafter, the product which precipitated during that time was removed by suction filtration and dried. Yield: 4.2 gm (0.011 mol; 73% of theory), M.p.: 221-224 C.

Statistics shows that 3,5-Dichloro-2,4-difluoroaniline is playing an increasingly important role. we look forward to future research findings about 83121-15-7.

Reference:
Patent; Celamerck GmbH & Co. KG; US4457943; (1984); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics