Author: Jessica.F

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

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. 21397-08-0, name is 2-Chloro-3-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H5ClFN

a) Compound 6.2; To a solution of aniline 6.1 (500 mg, 3.43 mmol) in acetic acid (4 mL) was added KI (820 mg, 4.94 mmol), NaBO3.4H2O (710 mg, 4.61 mmol) and (NH4)2MoO4 (710 mg, 3.62 mmol). After 30 min the reaction was poured into a mixture of saturated aqueous NaHCO3 solution (5 mL) and aqueous 10% Na2S2O3 solution (1 mL). The aqueous layer was extracted with Et2O and the combined organic phase were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to give compound 6.2 (860 mg, 92% yield) as a beige solid.

The synthetic route of 21397-08-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/69261; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 54730-35-7, name is 3,5-Dichloro-4-methylaniline, 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 54730-35-7, Product Details of 54730-35-7

Preparation 9; 5-bromo-l,3-dichloro-2-methylbenzene; Suspend 3, 5 -dichloro-4-methylaniline in 48percent HBr (5 mL) and water (5 mL) and heat with a heat gun until the mixture is near the boiling point. Cool the slurry to room temperature and then cool to 00C with an ice/brine bath. Add dropwise a solution of sodium nitrite (109 mg, 1.58 mmol) in water (2 mL). After the addition is complete, stir the reaction an additional 15 min in the cold bath. Add a solution of CuBr (1.08 g, 7.53 mmol) in 48percent HBr (2 mL) and heat the rapidly stirring reaction to 500C for 1 hour. Cool the reaction to room temperature, dilute with EtOAc and discard the aqueous layer. Wash the organic layer with water and brine, dry with MgSO4, filter through celite and concentrate to an orange residue. Purify the residue by silica gel chromatography eluting with hexanes to afford 164 mg (45percent) of the product as a yellow solid.

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; ELI LILLY AND COMPANY; WALLACE, Owen, Brendan; WO2007/127726; (2007); A2;,
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. 102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-5-chloro-2-methoxyaniline

This compound was prepared using a method analogous to that of 4-amino-2,5- dimethylbenzonitnle, 4-bromo-5-chloro-2-methoxyaniline replacing 4-bromo-2,5-dimethyl aniline except that the reaction mixture was stirred ON at 110C. LC-MS (A): tR = 0.76 min, [M+H]+: 183.19

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; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; RENNEBERG, Dorte; STAMM, Simon; WO2014/97140; (2014); 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. 454-78-4, name is 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

Examples 1 :1 – 1 :8 (Procedure A).A mixture of VII (0.32 mmol), the appropriate aryl bromide (0.38 mmol), CS2CO3, (146 mg, 0.448 mmol), BINAP (15 mg, 0.024 mmol), Pd(OAc)2 (3.6 mg, 0.016 mmol) and toluene (3 mL) was stirred at 100 0C for 7 h and at rt for 14 h. The mixture was filtered through Celite and the solids washed with EtOAc. Concentration of the combined filtrates gave ester VIII in yields given in Tabe 1.

According to the analysis of related databases, 454-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOLIPOX AB; WO2009/127822; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 928-50-7, A common heterocyclic compound, 928-50-7, name is 5-Chloropent-1-ene, molecular formula is C5H9Cl, 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 12 (S)-4-(1-Methylethyl)-3-(1-Oxo-4-Pentenyl)-2-Oxazolidinone To a -78 C. solution of 5.0 g of 4-(1-methylethyl)-2-oxazolidinone in 80 ml of tetrahydrofuran is added, dropwise, 15.5 ml of 2.5M n-butyl lithium in hexane. After stirring for 30 minutes, a solution of 4.8 g of 4-pentenyl chloride in 30 ml of tetrahydrofuran is added, dropwise, and the resulting solution is stirred at -78 C. for 3.5 hours. The reaction is diluted with aqueous ammonium chloride and diethyl ether. The organic layer is washed with water, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel, 25% ethyl acetate/petroleum ether) to give 5.8 g of the desired product as a pale yellow oil. [alpha]D26 =+79 (methylene chloride).

The synthetic route of 928-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US5550257; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics