Month: May 2021

Electric Literature of 174913-12-3, A common heterocyclic compound, 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, molecular formula is C7H6BrClO, 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.

Preparation 3 [3-CHLORO-5-METHOXVBENZONITRILE] Tetrakis (triphenylphosphine) palladium (0) (174 mg, 0.15 [MMOL)] was added in one portion to a stirred solution of the bromide of Preparation 1 (500 mg, 2.26 [MMOL)] and zinc cyanide (146 mg, 1.24 [MMOL)] [IN N, N-DIMETHYLFORMAMIDE] (3 ml) at room temperature under a nitrogen atmosphere. The reaction was heated at [100C] for 14 hours and then cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using ethyl acetate in cyclohexane as eluant (5: 95) to provide the title compound as a yellow oil (380 mg).1H-NMR [(300MHZ,] [CDC13)] : [8 3.] 82 (s, 3H), 7.04 (s, [1H),] 7.12 (s, [1H),] 7.23 (s, 1H).

The synthetic route of 174913-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/31178; (2004); 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. 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 63624-28-2

General procedure: To a solution of 0.5 mL of pyridine and 0.5 mmol of intermediate 5,20 mL of dried dichloromethane was added followed by 1 mmol of selectedsubstituted sulfonyl chlorides (a-k). The resulting reaction mixturewas refluxed for 12-17 h and reaction was monitored by TLC. Aftercompletion, the reaction mass was quenched using 20 mL of 10% NaOHfollowed by the extraction with chloroform with quantities 3×15 mL.The organic portion was then passed through anhydrous sodium sulfate,concentrated in vacuo and purified by column chromatography (DCM)to afford 7a-k.

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 63624-28-2.

Reference:
Article; Patel, Rahul V.; Mistry, Bhupendra M.; Syed, Riyaz; Parekh, Nikhil M.; Shin, Han-Seung; Bioorganic Chemistry; vol. 87; (2019); p. 23 – 30;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 771583-81-4, 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. 771583-81-4, name is 4-Chloro-2-(trifluoromethyl)benzylamine, This compound has unique chemical properties. The synthetic route is as follows.

5-((4- (ethylsulfonyl) benzyl) carbamoyl) -2-methoxybenzoic acid (150.0 mg, 0.4 mmol), HATU (302.2 mg, 0.8 mmol) and DIPEA (154.1 mg, 1.2 mmol) was dissolved in tetrahydrofuran (10 mL), and after stirring at room temperature for 0.5 hours, 4-chloro-2- (trifluoromethyl) benzylamine (125.0 mg, 0.6 mmol) was added, and the reaction was performed at room temperature for 4 hours. An appropriate amount of water was added and extracted three times with ethyl acetate. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (90.0 mg, yield: 38%).

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

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Chunchi; Liu Jinming; Ren Yun; Cai Jiaqiang; Wang Lichun; Wang Jingyi; (42 pag.)CN110724075; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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 1871-57-4, SDS of cas: 1871-57-4

[0129] A mixture of BnNH-L-Asp(Otbutyl)-Obn from step 1a (12.1 g, 32.6 mmol), K2CO3 (14 g, 3 eq.), NaI (3.0 g, 20mmol) and 1-chloro-2-chloromethyl-1-propene (5.1 g, 40.8 mmol) in MeCN (150 mL) was stirred at 81 C for 16 h. Aftercooling, the mixture was filtered. The filtrate was concentrated and purified by Combiflash (hexane and ethyl acetate:gradient 0 to 8% during 12 min) to give (8.7 g) 1-benzyl 4-tert-butyl (2S)-2-{benzyl[2-(chloromethyl)prop-2-en-1-yl]amino}succinate, MS (ESI): 458.3/460.3 (M + H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-chloromethyl-1-propene, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; YAO, Wenqing; ZHOU, Jincong; XU, Meizhong; ZHANG, Fenglei; METCALF, Brian; EP1622569; (2015); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2687-12-9,Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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.

General procedure: A representative procedure of skeleton 4 is as follows: K2CO3 (400 mg, 2.9 mmol) was added to a solution of 3 (1.0 mmol) in acetone (10 mL) at rt. The reaction mixture was stirred at rt for 10 min. Cinnamyl chloride (1.05 mmol) was added to the reaction mixture at rt. The reaction mixture was stirred at reflux for 8 h. The reaction mixture was cooled to rt, concentrated, and extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated to afford crude product under reduced pressure. Purification on silica gel (hexanes/EtOAc=6:1 to 1:1) afforded 4.

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chang, Meng-Yang; Lu, Yi-Ju; Cheng, Yu-Chieh; Tetrahedron; vol. 71; 8; (2015); p. 1192 – 1201;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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. Formula: C8H10ClN

EXAMPLE 22 Under a static nitrogen atmosphere at 0 C., a solution of n-butyllithium (7.87 g, 0.123 mol) in hexane was added to a solution of tetramethylethylenediamine (14.3 g, 0.123 mol) in 60 ml. of anhydrous cyclohexane with constant stirring. The resulting mixture was stirred for an additional 15 minutes and then cooled to -70 C. using a solid carbon dioxide-acetate bath. A solution of N-methyl-4-chloro-benzylamine (9.6 g, 0.06 mol) in 60 ml. of anhydrous cyclohexane was added to the reaction mixture to produce a suspension containing a dilithio compound. This suspension was stirred for 2 hours at 26 C. and then cooled to -70 C. using a solid carbon dioxide-acetone bath. A solution of phenylphosphonic dichloride (12.5 g, 0.064 mol) in 60 ml. of anhydrous cyclohexane was rapidly added to the suspension causing the temperature of the reaction to increase to -20 C. The reaction mixture was allowed to cool to -70 C., after which time the solid carbon dioxide-acetone bath was removed and the reaction mixture was stirred for 2.5 hours. The reaction mixture was cooled to 0 C. and then quenched with the rapid addition of 12 ml. of acetic acid. The cyclohexane was removed on a rotary evaporator, and the resulting residue was partitioned between methylene chloride and water. The layers were separated and the methylene chloride layer was dried over magnesium sulfate and concentrated in vacuo to yield a red oil. Distillation of the red oil at 180 C. and 0.25 mm yielded a yellow solid which was slurried in ether to yield 1-phenyl-2-methyl-6-chloro-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (2.2 g, 13% yield) as a pale yellow solid having a melting point of 159-162 C. and the following analysis: Calculated: C, 60.55; H, 4.72; N, 5.04. Found: C, 60.59; H, 4.72; N, 5.06.

The synthetic route of 1-(4-Chlorophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Monsanto Company; US4319913; (1982); A;,
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. 772-49-6, name is 1-Chloro-3-(trifluoromethoxy)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H4ClF3O

N,N-Di-isopropylamine (38.4 ml, 27lmmol) was added dropwise to a solution of nbutyllithium (1.6 M, 169 ml, 271 mmol) in THF (180 ml) at 0C and the reaction mixture was stirred and allowed to warm to room temperature over 30 mins. The LDA solution was then added drop wise over lOminutes to a solution of 1-chloro-3- (trifluoromethoxy)benzene (50 g, 246 mmol) in THF (500 ml) at -70C and the resultingmixture was stirred at -70C for 30 minutes. Finally N,N-dimethylformamide (23 ml, 296 mmol) was added dropwise and the resultant mixture stirred at -70C for 30 minutes.The reaction was quenched at -70C by addition of NH4C1 (saturated aqueous solution) to pH 7-8 and the resulting mixture was extracted with EtOAc (3 x 75 ml). The combined organic phases were washed with water (100 ml), brine (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound (55 g, 99% yield).LCMS (Method 16, ES+) RT 1.32 mm., 224 [M+H].

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:
Patent; UCB BIOPHARMA SPRL; SANOFI; DE HARO GARCIA, Teresa; DELIGNY, Michael; HEER, Jag Paul; QUINCEY, Joanna Rachel; XUAN, Mengyang; ZHU, Zhaoning; BROOKINGS, Daniel Christopher; CALMIANO, Mark Daniel; EVRARD, Yves; HUTCHINGS, Martin Clive; JOHNSON, James Andrew; JADOT, Sophie; KEYAERTS, Jean; MAC COSS, Malcolm; SELBY, Matthew Duncan; SHAW, Michael Alan; SWINNEN, Dominique Louis Leon; SCHIO, Laurent; FORICHER, Yann; FILOCHE-ROMME, Bruno; (365 pag.)WO2016/50975; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 53531-69-4, 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. 53531-69-4, name is (4-Bromophenyl)methanesulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Diethyl 5-aminobenzofuran-2,3-dicarboxylate (0.8 g, 2.59 mmol), 4-bromobenzylsulfonyl chloride (1.56 g, 5.77 mmol),Potassium carbonate (1.01 g, 7.30 mmol) was successively added to 30 mL of dichloromethane, and the mixture was stirred overnight at room temperature, and potassium carbonate was removed by filtration, and the residue was purified by column chromatography to yield 1.32 g (yield: 89.64%).

The synthetic route of (4-Bromophenyl)methanesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; You Qidong; Wei Jinlian; Jiang Zhengyu; Guo Xiaoke; Xu Xiaoli; Zhang Xiaojin; (44 pag.)CN107619384; (2018); 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. 452-83-5, name is 2-Chloro-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 452-83-5

2-Chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclopentylmethyl-amide (100mg Example 183a), 2-chloro-5-fluoroaniline (ex-Fluorochem, 237mg), and 1,4-dioxan (1 ml) were stirred at 100C under nitrogen for 18h. The cooled reaction mixture was evaporated in vacuo, treated with ethyl acetate (5 ml), washed with aqueous 2M hydrochloric acid (2 x 3ml), followed by water (2×3 ml), and dried (Na2SO4). The solution was evaporated in vacuo and the residue purified by mass directed autopreparative purification to give the title compound (35mg). NMR 8 (CDC13) 1.2-1. 35 (2H, m), 1.53-1. 76 (>4H, m + H20), 1.78-1. 90 (2H, m), 2. 17 (1H, q), 3.41 (2H, dd), 5.9 (1H, brt), 7.0-7. 11 (2H, m), 7.65-7. 7 (1H, m) 8.56 (1H, dd), 8.79 (1H, s). LC/MS t = 3.67 min, Molecular ion observed [MH 417 consistent with the molecular formula C18H17ClF4N4O.

According to the analysis of related databases, 452-83-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; DOUGHTY, Jennifer, Margaret; WO2005/74939; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 202197-26-0

General procedure: To a solution of 4-chloro-7-fluoro-6-nitroquinazoline (4.58 g,20 mmol) in acetonitrile (500 ml) was added 3-chloro-4-(3-fluorobenzyloxy)aniline (4.77 g, 19 mmol), and then the mixturewas raised to reflux. Once the reaction was completed as indicatedby TLC, The precipitate was collected by filtration, and washed withacetonitrile to give N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-7-fluoro-6-nitroquinazolin-4-amine 7.5 g (16.9 mmol, 85%)

The synthetic route of 202197-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Long; Yang, Yingying; Zhou, Haojie; Zheng, Qingmei; Li, Yuhao; Zheng, Shansong; Zhao, Shuyong; Chen, Dong; Fan, Chuanwen; European Journal of Medicinal Chemistry; vol. 102; (2015); p. 445 – 463;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics