Month: July 2021

Electric Literature of 6940-78-9, 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. 6940-78-9, name is 1-Bromo-4-chlorobutane belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 9; Preparation 7-CBQ by a Reaction of 7-HQ with 1-bromo-4-chlorobutane in 2-propanol in Presence of About 47% sodium hydroxide solution; A mixture of 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (4 g, 0.024 mole) and 1-bromo-4-chlorobutane (8.6 ml, 12.75 g, 0.073 mole, 3 eq.) in 2-propanol (20 ml) was refluxed followed by addition of mixture of about 47% aqueous sodium hydroxide solution (2.5 g, 0.029 mole, 1.2 eq.) and 2-propanol (4 ml). Reflux was continued for 2 hours. The hot reaction mixture was filtered, and the solvent and an excess of 1-bromo-4-chlorobutane were removed to dryness in vacuum. 2-propanol (12.5 ml) was added to the residue thus obtained and the mixture was refluxed to obtain a solution, followed by addition of a solution of 47% aqueous sodium hydroxide to produce a pH of about 10-11. The mixture was set aside at 10-15 C. for 6 hours. A colorless precipitate was collected by filtration, washed with cold mixture of water and 2-propanol (1:3, 7 ml) and water (10 ml). The solid was dried under reduced pressure at 50 C. overnight to obtain 7-(4-chlorobutoxy)-3,4-dihydro-2(1H)-quinolinone (5.55 g) in 89.2% yield, having a purity of 98.2% (by HPLC).

The synthetic route of 1-Bromo-4-chlorobutane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Naddaka, Vladimir; Brand, Michael; Davidi, Guy; Klopfer, Eyal; Gribun, Irina; Arad, Oded; Kaspi, Joseph; US2006/79689; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, 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. Recommanded Product: 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine

Synthesis of 2-chloro-8-(4-fluorobenzyl)-7 , 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0440] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (100 mg, 0.58 mmol) in DMF (1 mL) under argon atmosphere was added sodium hydride (27 mg, 1.16 mmol) at 0 C. After stirring for 10 mins, l-(bromomethyl)-4-fluorobenzene (132 mg, 0.70 mmol) was added at 0 C and stirred for 1 h. After consumption of the starting materials (monitored by TLC), the reaction was quenched with ice water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford 2-chloro-8-(4-fluorobenzyl)-7, 8-dihydro- 6H-pyrimido [5, 4-b] [1, 4] oxazine (150 mg, 92%) as an off-white solid. 1H-NMR (DMSO- d6, 400 MHz): delta 7.70 (s, 1H), 7.36 (t, 2H), 7.18 (t, 2H), 4.75 (s, 2H), 4.19-4.16 (m, 2H), 3.51- 3.48 (m, 2H); LCMS: 279.9 (M+1); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.59 min 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 60% EtOAc/hexane (R 0.5).

The synthetic route of 1303587-99-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 461432-23-5, These common heterocyclic compound, 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, 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.

Under nitrogen, to a 50mL three-necked flask were added sequentially 3.99g2- chloro-5-bromo-ethoxy -4`- – diphenylmethane, 10ml of tetrahydrofuran and 30ml of toluene, followed by stirring to dissolve, cooled to -78 deg.] C, was added dropwise 2.4M n-hexane solution of n-butyllithium in 5.48ml, dropping the temperature was kept below -70 deg.] C, after the addition was complete the reaction was complete to give 2-chloro-5-ethoxy-lithium -4`- – diphenyl methane solution. Under nitrogen atmosphere, into a three-necked 250mL flask was added 8.43g Compound B-2 and 40ml of toluene, followed by stirring to dissolve, cooled to -78 deg.] C, the lithium-chloro-5-ethoxy -4`- – diphenylmethane was added dropwise, the dropping rate to keep the temperature below -65 deg.] C, after the addition was complete the reaction was kept 2 hours, 17.63g of tetrabutyl ammonium fluoride was added dropwise, the reaction was stirred for 1 hour at room temperature, methanol was added dropwise a solution of 7.45g of sulfuric acid ( containing 2.56 g of sulfuric acid), after the completion of the dropwise addition, the reaction mixture was stirred at room temperature, the HPLC monitoring of the reaction is complete, add saturated NaHCO3 solution to a pH of about 7.5, the organic layer was separated and the aqueous layer extracted with ethyl acetate, the combined organic phases were washed with saturated brine washed with water, vacuum distillation, additional 20ml toluene, evaporated under reduced pressure rotary evaporation to give 4.16g of intermediate -1, yield: 77.3%.

Statistics shows that 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene is playing an increasingly important role. we look forward to future research findings about 461432-23-5.

Reference:
Patent; Beijing Wan-sheng Pharmaceutical Co., Ltd.; Lin, Guoliang; Li, Xiaopeng; Liu, Zhidong; Wang, Zhanwei; Li, Yong; Pei, Yingzi; (15 pag.)CN105481915; (2016); A;,
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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H4Cl3NO

General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid.

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 2533-69-9.

Reference:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 97329-43-6, name is 1-Bromo-2-chloro-3-methylbenzene, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

General procedure: A mixture of arylaldehyde (0.1 g, 1 mmol), dihaloarene (0.565 g, 2 mmol), Pd(OAc)2 (0.022 g, 10.0 mol%), N-phenylpicolinamide (L7, 0.019 g, 15.0 mol%) and potassium hydrogen carbonate (0.5 g, 5 mmol) in tert-amyl alcohol (5.0 ml) was taken in 100.0 ml round bottom flask under N2 atmosphere and stirred for 120C for 24 h. Progress of the reaction was monitored continuously by TLC with ethyl acetate: hexane (2:3) eluent system. After completion of reaction, crude was poured into crushed ice and then filter the reaction mixture. Filtrate then extracted with ethyl acetate (3 times). Organic layer was separated, dried (over anhydrous Na2SO4) and evaporated under reduced pressure and purified by column chromatography to obtain desired product. Characterization data of compounds 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3v and 3x were found exactly similar as reported in the literature (References of above compound are mentioned in Supplementary data).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Patel, Anuj; Shaikh, Mahommedumar; Chikhalia, Kishor; Tetrahedron; vol. 75; 2; (2019); p. 236 – 245;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 16793-91-2, 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. 16793-91-2, name is 2-Chlorophenethyl Bromide, This compound has unique chemical properties. The synthetic route is as follows.

Example 58 Preparation of 6-(2-chlorophenethyl)-1.2.3.4.5.6-hexahvdro-3.9- dimethylazepmor4.5-b1mdole (Compound No 69)[0423] The title compound was prepared by following general procedure 4 3,9-Dimethyl- l,2,3,4,5,6-hexahydroazepmo[4,5-b]mdole (214 mg, 1 0 mmol) was taken with copper iodide(19 mg, 0 1 mmol), L-pralme (23 mg, 0 2 mmol), potassium phosphate t?basic (426 mg, 2 0 mmol), l-(2-bromoethyl)-2-chlorobenzene (219 mg, 1 0 mmol) and DMF was added, the reaction was stirred at 900C under argon atmosphere for 12 h and monitored by LCMS After completion of the reaction water was added and extracted with ethyl acetate The organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum The crude product was purified by reverse phase chromatography to afford 50 mg of the title compound (10 7%)

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

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; HUNG, David, T.; PROTTER, Andrew, Asher; JAIN, Rajendra, Parasmal; CHAKRAVARTY, Sarvajit; GIORGETTI, Marco; WO2010/51503; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 933190-51-3, These common heterocyclic compound, 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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.

To a solution of 6-(piperidin-1-yl)pyridin-2-amine (0.725 g, 4.12 mmol) in DMF (8 mL) was added NaH (0.11 g, 60% dispersion in mineral oil, 4.18 mmol) and the mixture stirred for 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (0.384 g, 1.65 mmol) under N2. The mixture was stirred at room temperature for 16 h. The resulting mixture was treated with a saturated NH4Cl solution (50 mL), extracted with ether (80 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give 6-chloro-N-(6-(piperidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (0.13 g, 24.1%) as a yellow solid. LC-MS: [M+H]+, 329.0, 331.0, tR=1.912 min

Statistics shows that 8-Bromo-6-chloroimidazo[1,2-b]pyridazine is playing an increasingly important role. we look forward to future research findings about 933190-51-3.

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
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 67330-62-5 as follows. Quality Control of 3-Chloro-2,6-diethylaniline

A mixture of 7-hydroxynaphthalene- 1,3 -disulfonyl dichloride (255 mg, 0.75 mmol) and 2,6-diethylaniline (550 mg, 3.0 mmol) in acetonitrile (3 mL) was heated under reflux during 4 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (30 mL). The extract was washed with 4% HCl (30 mL), dried with Na2SO4, evaporated and purified by chromatography (petroleum ether- ethylacetate, 2:1). Yield 21 mg (4%), as a white powder, mp 142-144 C.1H NMR (DMSO-^), delta: 0.75-0.98 (m, 12H); 2.05-2.46 (m, 8H); 7.09 (dd, J = 8.4,2.1 Hz5 2H); 7.32 (d, J = 8.4 Hz5 2H); 7.38 (dd, J= 9.0, 2.2 Hz5 IH); 7.94 (d, J =2.2 Hz5 IH); 8.19 (d, J = 9.1 Hz, IH); 8.28 (d, J= 1.9 Hz, IH); 8.45 (d, J = 1.9 Hz, IH); 9.78 (s, IH); 10.01 (s, IH); 10.65 (s, IH).

According to the analysis of related databases, 67330-62-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOLIPOX AB; WO2007/42817; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, 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 13918-92-8, HPLC of Formula: C6H3ClF2O2S

[00201] To a solution of 5-bromo-2-chloro-4-methylpyridin-3-amine (12 g, 54 mmol) in THF (360 niL) was added a 1.0 M solution of LiHMDS in THF (108 niL, 108 mmol) at -5C. The reaction mixture was allowed to stir at -5C for 10 mm. To the reaction mixture was then added 2,4- difluorobenzenesulfonyl chloride (17.3 g, 81 mmol). The reaction mixture was allowed to stir at ii for 12 h. The reaction mixture was diluted with saturated NFI4C1 solution (200 mL) and extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The crude compound was purified by column chromatography to provide N-(5-bromo-2-chloro-4-methylpyridin-3-yl)-2,4- difluorobenzenesulfonamide (11.5 g, 53%). ?H NMR (400 MFIz, CDC13) 6 8.37 (s, in), 7.72 (m, in), 7.00 (m, 2H), 6.70 (s, in), 2.64 (s, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; WONG, Tzu-Tshin; XU, He; XU, Tianlin; YE, Yingchun; WO2015/108861; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 61881-19-4, 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 61881-19-4 as follows.

A solution of isomaltose (100 mg, 0.292 mmol) in dry pyridine(2.0 mL) was treated with acetic anhydride (0.8 mL) and 4-(N,Ndimethylamino)pyridine (5 mg) at 0 C and after 20 h at ambienttemperature, excessive reagent was destroyed by adding dry MeOH(2.0 mL) at 0 C. After 10 min the solvent was coevaporated withtoluene (3×) and the residual oil was purified by chromatography(n-hexane/EtOAc 1:1 ? 1:2) affording an alpha/beta-mixture (1:1) ofperacetylated isomaltose (198 mg, quantitative yield). The residue(101 mg, 0.149 mmol)was dissolved in dry DMF (2.0 mL) and treatedwith hydrazine acetate (27 mg, 0.298 mmol) at 40 C for 2 h underAr. The mixture was diluted with EtOAc, washed with cold brineand the organic layer was dried (MgSO4) and filtered. Concentrationof the filtrate provided a crude product, which was purifiedby chromatography (n-hexane/EtOAc 1:2) to obtain an alpha/beta-mixture (1:0.3) of the hemiacetal (85 mg, 90%): 1H NMR (CDCl3): delta5.53 (dd, 1H, J3alpha,2alpha 10.1, J3alpha,4alpha 9.4 Hz, H-3alpha), 5.46 (app t, 1H, J3?beta,2?beta ~ J3?beta,4?beta9.8 Hz, H-3?beta), 5.45 (app t, 1H, J3?alpha,2?alpha ~ J3?alpha,4?alpha 9.8 Hz, H-3?alpha), 5.40(app t, 1H, J1alpha,2alpha ~ J1alpha,OH 3.5 Hz, H-1alpha), 5.23 (app t, 1H, J3beta,2beta ~ J3beta,4betaHz, H-3beta), 5.14 (d, 1H, J1?beta,2?beta 3.8 Hz, H-1?beta), 5.13 (d, 1H, J1?alpha,2?alpha3.8 Hz, H-1?alpha), 5.02-4.97 (m, 3H, H-4?alpha, H-4beta, H-4alpha), 4.94 (dd, 1H,J4alpha,5alpha 10.3 Hz, H-4alpha), 4.85-4.78 (m, 4H, H-2alpha, H-2?alpha, H-2beta, H-2?beta),4.73 (app t, 1H, J 8.0 Hz, H-1beta), 4.24 (ddd, 1H, J5alpha,6aalpha 6.5, J5alpha,6balpha2.5 Hz, H-5alpha), 4.21-4.05 (m, 7H, H-5?alpha, H-5?beta, H-6?aalpha, H-6?abeta,H-6?balpha, H-6?bbeta, OHbeta), 4.02-3.99 (m, 1H, OHalpha), 3.74-3.57 (m,5H, H-5beta, H-6aalpha, H-6abeta, H-6balpha, H-6bbeta), 2.10 to 2.00 (10 s, 14×COCH3); ESI-TOF HRMS: m/z = 659.1794; calcd for C26H36O18Na+:659.1798.The residue (70 mg, 0.110 mmol) was dissolved in dry CH2Cl2(1.8 mL) and dry acetone (1.0 mL). Potassium carbonate (30 mg,0.220 mmol) and 2,2,2-trifluoro-N-phenylacetimidoyl chloride (35 muL,0.220 mmol) were added successively under Ar. The suspension wasstirred for 12 h at rt, then filtered through a pad of Celite, rinsedwith CH2Cl2 and the filtrate was concentrated. Swift chromatographicpurification (n-hexane/EtOAc 1:1) provided 17 (80mg, 90%)which was directly used for the subsequent glycosylation reaction.1H NMR spectra of 17 (CDCl3) displayed broad signalscorresponding to a 2.5:1 mixture; 13C NMR (125 MHz, CDCl3, selecteddata): delta 169.8-168.9 (C = O, Ac), 142.8, 128.9, 128.8 124.7 and119.4 (arom. C), 96.0 (C-1, C-1?), 66.4 and 66.2 (C-6), 61.7 (C-6?), 20.6-20.4 (CH3CO).

According to the analysis of related databases, 61881-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pokorny, Barbara; Kosma, Paul; Carbohydrate Research; vol. 422; (2016); p. 5 – 12;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics