Category: chlorides-buliding-blocks

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 63624-28-2 as follows. Application In Synthesis of 2,4-Dimethoxybenzene-1-sulfonyl chloride

620 mg of the compound obtained in step 15-1 (diastereoisomer mixture) was added under ice cooling and a nitrogen atmosphere to a 10 mL N,N-dimethylformamide solution of 67 mg of sodium hydride, and the reaction mixture was stirred for 40 minutes. After this, a 2 mL N,N-dimethylformamide solution of 400 mg of 2,4-dimethoxybenzenesulfonyl chloride was added dropwise. The reaction mixture was stirred for 30 minutes at the same temperature, after which 5 mL of ethyl acetate and 10 mL of a 5% potassium carbonate aqueous solution were added, and the reaction mixture was stirred at room temperature overnight. The precipitated solids were filtered off and separated and purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/acetone = 99/1; v/v) to obtain two kinds of diastereoisomer of the titled compound in amounts of 184 mg (isomer A: colorless, amorphous) and 256 mg (isomer B: colorless, amorphous). Isomer A: [alpha]D25 = -225 (c = 0.187, chloroform) MS (ESI pos.) m/z : 612([M+H]+), (ESI pos.) m/z : 634([M+Na]+) 1 H-NMR (499 MHz, CDCl3) delta (ppm) ; 1.53 – 1.62 (m, 1 H), 1.85-1.98 (m, 1 H), 2.18 – 2.32 (m, 7 H), 2.75 (s, 3 H), 3.10-3.25 (m, 1 H), 3.55-3.86 (m, 9 H), 4.89-5.01 (br, 1 H), 5.21 – 5.39 (m, 1 H), 6.40 (d, J=1.8 Hz, 1 H), 6.58 (dd, J=9.0, 2.3 Hz, 1 H), 6.76 (d, J=7.9 Hz, 1 H), 6.85 – 6.97 (m, 2 H), 7.07 (dd, J=8.5, 1.2 Hz, 1 H), 7.17 – 7.24 (m, 1 H), 7.74 – 7.84 (m, 2 H), 8.15 (d, J=8.8 Hz, 1 H) Isomer B: [alpha]D25 =+142 (c = 0.240, chloroform) MS (ESI pos.) m/z : 612([M+H]+), (ESI pos.) m/z : 634([M+Na]+) 1 H-NMR (499 MHz, CDCl3) delta (ppm) ; 1.81 – 1.96 (m, 1 H), 2.11 – 2.23 (m, 4 H), 2.46 (s, 3 H), 2.62 (s, 3 H), 3.24 (s, 3 H), 3.36 – 3.49 (m, 1 H), 3.73 – 3.87 (m, 7 H), 4.06-4.11 (m, 1 H), 5.00 – 5.15 (m, 1 H), 6.47 (d, J=2.4 Hz, 1 H), 6.60 (dd, J=9.0, 2.3 Hz, 1 H), 6.66 – 6.73 (m, 2 H), 7.03 – 7.10 (m, 2 H), 7.18 – 7.24 (m, 1 H), 7.81 (d, J=8.2 Hz, 1 H), 8.15-8.25 (m, 2 H)

According to the analysis of related databases, 63624-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1659121; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 61881-19-4, A common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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.

Compound II – 1 (200 mg, 0 . 187 mmol), N – benzene three fluorine second grades acyl chloride (116 mg, 0 . 56 mmol, 3 eq) dissolved in 5 ml acetone, batches adding potassium carbonate (77 mg, 0 . 56 mmol, 3 eq), stirring at room temperature 1 hour (TLC detection consumption end), filtering, the filtrate turns on lathe does, column to obtain white solid (229 mg, yield 99%)

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; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Lin Feng; Lu Rui; Xu Qiulong; Chen Jianli; Han Jine; (33 pag.)CN104231009; (2017); B;,
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. 870-24-6, name is 2-Chloroethanamine hydrochloride, A new synthetic method of this compound is introduced below., name: 2-Chloroethanamine hydrochloride

In a first reaction step, 3-chloroethylamine hydrochloride (73.86 g, 0.70 mol, 1.00 eq) is initially charged in ethanol (3.0 l) in a 4 l three-neck flask with precision glass stirrer, internal thermometer, dropping funnel and reflux condenser, and cooled to -78 C., and sodium ethoxide (226.83 g, 0.70 mol, 1.00 eq, 21% in ethanol) is added. 3-Isocyanatopropyl(triethoxysilane) (173.15 g, 0.70 mol, 1.00 eq) is then added dropwise at -78 to -70 C. within 3 h and then the mixture is heated to 50 C. Dry sodium sulphide (Na2S, 27.31 g, 0.35 mol, 0.50 eq) is added in five portions and the mixture is heated to reflux. After a reaction time of 4 h, the mixture is cooled to room temperature and the suspension is filtered. The filtrate is freed of the solvent on a rotary evaporator and dried under reduced pressure. The (EtO)3Si-CH2CH2CH2-NH-CO-NH-CH2CH2-S-CH2CH2-NH-CO-NH-CH2CH2CH2-Si(OEt)3 product (212.68 g, 98.8% of theory) is obtained as a yellow oil.

The synthetic route of 870-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Evonik Industries AG; Moser, Ralph; Mayer, Stefanie; (10 pag.)US2015/329571; (2015); 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. 363-51-9, name is 2-Chloro-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 363-51-9

To the solution of H(3-(trifiuoFomethyl phenyf)sulfonyl)indolirte-6-carboxyiic acid (50 mg, 0.13 mmol): in 1 mi of anhydrous THF at 0 C were added oxayl chloride (23 pL, 0.27 mmol) and a drop of DMF. The reaction was stirred at room temperature for l b. The completion of the reaction was monitored by HPLC, Upon completion, the solvent was removed in vacuo. To the crude residue was added 1 mL of anhydrous THF and 2~chloro-6-fiuoroaniline (78 mg, 0.54 mmol). The reaction was stirred at 55 C for 2h. The completion of the reaction was monitored by HPLC. Upon completion, the solvent was removed in vacuo. The crude product was purified by preparative HPLC (20-100% CH3CN/MeOH (1 :1 ) in H20 (0.01% TFA)) which provided after lyophilization 40 mg (60%) of the title compound as a colorless -solid; 1H NMR (400 MHz, CDCi3) 6 – 8 14 (d, J = 1.3 Hz, 1 H), 8.12 (s, 1 H), 8.02 {d, J – 7.8 Hz, 1 H), 7.85 (d, J ~ 7.1 Hz, 1 H), 7.67 – 7.61 (m, 2 H), 7.59 (s, 1 H), 7.32 – 7,21 (m, 3 H), 7.18 – 7.10 (m, 1 H), 4.02 (1, J – 8,5 Hz, 2 H), 3.03 (1, J = 8.5 Hz, 2 H). MS (Epsilon5Gamma) m/z; 499,02 [M+H+]

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 363-51-9.

Reference:
Patent; THE SCRIPPS RESEARCH INTITUTE; GRIFFIN, Patrick, R.; KAMENECKA, Theodore, M.; DOEBELIN, Christelle; CHANG, Mi, Ra; (109 pag.)WO2018/52903; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1205-71-6, name is 4-Chloro-N-phenylaniline, 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. COA of Formula: C12H10ClN

Example 1.106: Preparation of Sodium 2-(((lr,4r)-4-(((4- Chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetate.; Method 1.; Step A: Preparation of ((lr,4r)-4-(hydroxymethyl)cyciohexyI)methyl 4- chlorophenyl(phenyl)carbamate.; 4-Chloro-N-phenylaniline (15.0 g, 73.6 mmol), tribasic potassium phosphate, (fine powder, 4.69 g, 22.1 mmol), N^V-carbonyldiimidazole (13.14 g, 81 mmol) and acetonitrile (75 mL) were charged to a 500-mL, jacketed, four-necked cylindrical reaction flask equipped with a mechanical stirrer and a condenser. The reaction mixture was heated at 65 0C under nitrogen and monitored by HPLC. After about 2.5 h HPLC showed > 98% conversion to the intermediate N-(4-chlorophenyl)-N-phenyl-lH-imidazole-l-carboxamide. After about 5.5 h a solution of (lr,4r)-cyclohexane-l,4-diyldimethanol (37.2 g, 258 mmol) in acetonitrile (150 mL) at 65 0C was added to the reaction mixture over 20 min. The resulting mixture was heated at 65 0C overnight. etaPLC showed about 98% conversion to the required product. The mixture was filtered, and the cake was rinsed with acetonitrile (2 x 25 mL). The filtrate was concentrated under reduced pressure (40 0C, 32 torr) 124.125 g of distillate was collected. The residue was diluted with water (50 mL) and this mixture was concentrated under reduced pressure (400C, 32 torr) and 35.184 g of distillate was collected. The residue was diluted with water (50 mL) and the resulting mixture was allowed to stir overnight to give a white paste. The mixture was filtered, and the cake was rinsed with 25% acetonitrile/water (2 x 75 mL). The solid was dried in a vacuum oven to leave a white solid (22.271 g); 94.8% purity by etaPLC peak area. LCMS m/z = 374.3 [M+eta]+; 1H nuMR (400 MHz, DMSO-^6) delta ppm 0.77 – 0.93 (m, 4 H) 1.23 (dd, J = 6.22, 3.51 Hz, 1 H) 1.47 (dd, J = 6.32, 2.91 Hz, 1 H) 1.56 – 1.76 (m, 4 H) 3.20 (t, J= 5.78 Hz, 2 H) 3.92 (d, J = 6.13 Hz, 2 H) 4.33 (t, J = 5.31 Hz, 1 H) 7.28 – 7.35 (m, 5 H) 7.38 – 7.47 (m, 4 H).

The synthetic route of 1205-71-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/117095; (2009); A1;,
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. 108-70-3, name is 1,3,5-Trichlorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H3Cl3

To a 250 ml one-necked flask was added 10.0 g (55.1 mmol) of 1,3,5-trichlorobenzene and 100 ml of ultra-dry tetrahydrofuran under argon gas protection and minus 78 degrees Celsius. Then, 23 ml (2.4 M, 55.2 mmol) of n-butyllithium in n-hexane was added dropwise, and the mixture was stirred at minus 78 C for 30 minutes. Then, 7.44 ml (107.3 mmol) of ultra-dry DMF was added dropwise, and stirring was continued for 1.5 hours at minus 78 C. The reaction was then slowly warmed to room temperature and quenched by the addition of 200 mL (3M) hydrochloric acid. The combined organic layers were washed with brine (25 mL) After evaporating the solvent, it was purified by column chromatography using methylene chloride: petroleum ether 1:1 (yield ratio) as eluent to afford 11.0 g of product A1, yield 95%.

The synthetic route of 108-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin University; Li Feng; Ai Xin; Zhang Ming; (25 pag.)CN108191739; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 6781-98-2, 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 6781-98-2 as follows.

General procedure: Under N2 atmosphere, KOtBu (114.0 mg, 1.0 mmol), NHC-Pd(II)-Im complex 1 (5.2 mg, 1.0 mol percent), dry toluene (1.0 mL), chlorobenzene 2a (0.8 mmol), and aniline 3a (0.96 mmol) were successively added into a Schlenk reaction tube. The reaction mixture was stirred under reflux for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by a flash chromatography on silica gel to give the pure product 4a.

According to the analysis of related databases, 6781-98-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhu, Lei; Ye, Yue-Mei; Shao, Li-Xiong; Tetrahedron; vol. 68; 10; (2012); p. 2414 – 2420;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1939-99-7, name is Phenylmethanesulfonyl 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 1939-99-7, Formula: C7H7ClO2S

A solution of phenylmethanesulfonyl chloride (2.19 g, 10 mmol) was added into a suspension of 3-bromopropan-l-amine hydrobromide (2.19 g, 10 mmol) and Et3N (2.02 g, 20 mmol) in THF (50 mL) at 0 C. The mixture was stirred at 0 C for 5 min. TLC confirmed the completion of reaction. Solid was filtered out with suction, and the filtrate was concentrated to provide compound N-(3- bromopropyl)(phenyl)methanesulfonamide (2.7 g, quant.) as a pale yellow solid which was used in the next step without further purification. NMR (300 MHz, CDC13) delta 7.40 (m, 5H), 4.48 (m, IH), 4.27 (s, 2H), 3.41 (t, J = 6.6 Hz, 2H), 3.16 (q, 2H), 2.01 (m, 2H). LCMS (ESI), m/z, 314 and 316 [M+Na]+, Br pattern found.

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, Phenylmethanesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; LADDYWAHETTY, Tammy; RENE, Olivier; (105 pag.)WO2016/96936; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 59681-66-2, name is 4-Chloro-N1-methylbenzene-1,2-diamine, molecular formula is C7H9ClN2, 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. Product Details of 59681-66-2

General procedure: A solution of compound 5 (R1=H, 100mg, 0.657mmol), 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea 6 (209mg, 0.722mmol), and p-toluene sulfonic acid (12mg, 0.065mmol) in isopropanol was heated at 65C for 16h. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate. The organic layer was successively washed with 1N sodium hydroxide and brine, and dried over sodium sulfate. After concentration in vacuo, the crude product was purified by silica gel column chromatography (eluent : n-Hex/EA=5 : 1) to give the compound 7 (R1=H, 121mg, yield 75%) as solid. 1H NMR (400MHz, DMSO-d6) delta 11.9 (NH, 1H), 7.38 (m, 2H), 7.14 (m, 2H), 3.65 (s, 3H), 1.45 (s, 9H); LC/MS (electrospray) m/z (M+H)+ 248.03.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59681-66-2, its application will become more common.

Reference:
Article; Windisch, Marc Peter; Jo, Suyeon; Kim, Hee-Young; Kim, Soo-Hyun; Kim, Keumhyun; Kong, Sunju; Jeong, Hyangsuk; Ahn, Sujin; No, Zaesung; Hwang, Jong Yeon; European Journal of Medicinal Chemistry; vol. 78; (2014); p. 35 – 42;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 76958-07-1, 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 76958-07-1 as follows.

[00378] N-[(6-chloro-1 ,3-benzodioxol-5-yl)carbamothioyl]benzamideImage available on “Original document”[00379] To 1 .88g ( 0.025 mol) of anhydrous ammonium thiocyanate in 40 ml acetone was added dropwise 3.2 g (0.023 mol) of benzoyl chloride. The resulting mixture was heated to reflux. Heating was removed and a solution of 3.8g (0.022 mol) of the amine in 15 ml dry acetone was added at a rate to maintain the mixture at boiling. After an additional 15 minutes reflux the reaction was cooled and the precipitate was filtered off. The precipitate was washed with acetone and dried to yield 5.5 g of the product.

According to the analysis of related databases, 76958-07-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KINEATA INC; Ladonato, Shawn P.; Bedard, Kristin M.; Munoz, Ernesto J.; Imanaka, Myra W.; Fowler, Kerry W.; (122 pag.)WO2014/113492; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics