Month: May 2021

Synthetic Route of 39191-07-6,Some common heterocyclic compound, 39191-07-6, name is 1-(3-Chlorophenyl)-N-methylmethanamine, molecular formula is C8H10ClN, 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: 2-(omega-Bromoalkyl)-isoindoline-1,3-dione (1 equiv) with N-methylbenzylamine (1 equiv) or its substituted analog in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 16 h. Once the reaction was finished, the solvent was evaporated under vacuum, producing a residue that was further dissolved in 50 mL of 5 M NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane to dichloromethane/methanol 98:2), yielding a yellow oil. The final product was obtained in the form of hydrochloride salt. The following compounds were obtained.

The synthetic route of 39191-07-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guzior, Natalia; Bajda, Marek; Rakoczy, Jurand; Brus, Boris; Gobec, Stanislav; Malawska, Barbara; Bioorganic and Medicinal Chemistry; vol. 23; 7; (2015); p. 1629 – 1637;,
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Synthetic Route of 1939-99-7,Some common heterocyclic compound, 1939-99-7, name is Phenylmethanesulfonyl chloride, molecular formula is C7H7ClO2S, 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.

K2C03 (8.7 g, 62 mmol) was added into a mixture of phenylmethanesulfonyl chloride (6 g, 31 mmol) and 2-bromoethanamine hydrobromide (6.4 g, 31 mmol) in DCM (100 mL) at 0C. And the resulting mixture was stirred at r.t. for 4 hours and left standing overnight. Upon the completion of reaction, water (100 mL) was added in and DCM phase was separated. The aqueous phase was extracted with DCM. The combined organic phase was dried over Na2S04, filetered and concentrated in vacuo to provide a crude which was separated with column chromatography (silica gel with 200 – 300 mesh, 0 to 50% of EtOAc in petroleum ether) to provide compound A^-(2-bromoethyl)(phenyl)methanesulfonamide (7.0 g, 80%) as a pale yellow solid. lU NMR (300 MHz, CDC13) delta 7.40 (m, 5H), 4.58 (m, 1H), 4.29 (s, 2H), 3.34-3.29 (m, 4H). LCMS (ESI), 300, 302 [M+Na]+, Br pattern found.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; GANCIA, Emanuela; LADDUWAHETTY, Tammy; VESEY, David; WINSHIP, Paul; RENE, Olivier; (168 pag.)WO2017/5900; (2017); A1;,
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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. 112-26-5, name is 1,2-Bis(2-chloroethoxy)ethane, A new synthetic method of this compound is introduced below., Formula: C6H12Cl2O2

Potassium carbonate (11.0g, 79.3mmol) in the presence of, at 50 , 4- hydroxythiophenol (1e) (10.0g, 79.3mmol) and 1,2-bis (chloroethoxy) ethane ( the reaction 7.06g, 37.76mmol) in place in DMAc35ml. using ethyl acetate / water system after the separating operation was performed to obtain crystals of the diol was purified by column (2b) (5.7g, 42%).

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; Fuji Photo Film Co., Ltd.; Song, Shantashi; Jia, tengjunye; (56 pag.)CN104159996; (2016); B;,
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Reference of 220227-21-4, A common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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.

General procedure: To a solution of A/-(2,4-dimethoxybenzyl)-3-methyl-1 ,2,4-thiadiazol-5- amine (1.14 g, 4.30 mmol) in tetrahydrofuran (20 mL) was added lithium N’s(trimethylsilyl)amide (1 M solution in tetrahydrofuran, 4.3 mL, 4.3 mmol) at -78 C. The reaction mixture was stirred for 30 minutes at 0 C and a solution of 2,4,5- trifluorobenzenesulfonyl chloride (0.99 g, 4.30 mmol) in tetrahydrofuran (10 mL) was added dropwise at -78 C. After the addition was complete, the cooling bath was removed. The reaction mixture was stirred for 3 h at ambient temperature and saturated aqueous ammonium chloride (10 mL) was added. The mixture was extracted with ethyl acetate (2 x 30 mL). The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford A/-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-A/-(3-methyl- 1 ,2,4-thiadiazol-5-y)benzenesulfonamide in 42% yield (0.83 g) as a colorless solid: MS (ES+) m/z 459.8 (M + 1).

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; XENON PHARMACEUTICALS INC.; SUN, Shaoyi; ZENOVA, Alla, Yurevna; CHAFEEV, Mikhail; JIA, Qi; ZHANG, Zaihui; OBALLA, Renata, Marcella; WO2013/64983; (2013); A1;,
Chloride – Wikipedia,
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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. 328-84-7, name is 3,4-Dichlorobenzotrifluoride, A new synthetic method of this compound is introduced below., Recommanded Product: 3,4-Dichlorobenzotrifluoride

PRODUCTION EXAMPLE 4 Production of an Intermediate Aniline Compound 3.00 Grams of 2,5-difluoro-4-mercaptoaniline hydrochloride, 6.60 g of 3,4-dichlorobenzotrifluoride and 4.90 g of potassium carbonate were dissolved in 30 ml of dimethylformamide, and the resulting solution was stirred for 6 hours at a temperature of from 100 to 110 C. in an oil bath. Thereafter, the reaction solution was poured into water and extracted with three 100-ml portions of diethyl ether. The extract obtained was washed with water, dried, filtered and concentrated. The residue obtained was subjected to chromatography on silica gel to obtain 3.60 g of 2,5-difluoro-4-[2-chloro-4-(trifluoromethyl)phenylthio]aniline. Yield 69% m.p. 95.9 C. 1 H-NMR (CDCl3):

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; Sumitomo Chemical Company, Limited; US5116875; (1992); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 5719-08-4, These common heterocyclic compound, 5719-08-4, name is 4-Chloro-9H-pyrimido[4,5-b]indole, 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.

General procedure: To a 100 mL round bottom flask were added appropriate 4-chloro-pyrimido[4,5-b]indole 11 or 12 (1 equivalent), 4-methoxy-N-methylaniline (4 equivalents), conc. HCl (2 drops), and BuOH (25 mL). The reaction mixture was heated to reflux for 72 h. After cooling to rt, silica gel (500 mg) was added, and BuOH was removed under reduced pressure to afford a silica gel plug. The plug was transferred on top of a column packed with silica gel, 20 times the weight of plug, and was eluted with 0.5% and 1% MeOH in CHCl3. Fractions containing the product (TLC) were pooled, and the solvent was evaporated to afford target compounds 2 or 3.

Statistics shows that 4-Chloro-9H-pyrimido[4,5-b]indole is playing an increasingly important role. we look forward to future research findings about 5719-08-4.

Reference:
Article; Devambatla, Ravi Kumar Vyas; Li, Wei; Zaware, Nilesh; Choudhary, Shruti; Hamel, Ernest; Mooberry, Susan L.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3423 – 3430;,
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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. 694-80-4, name is 1-Bromo-2-chlorobenzene, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-2-chlorobenzene

Sub 1-I-I-32 (109.66 g, 543.8 mmol) obtained in the above-Was placed in a round bottom flask,1-bromo-2-chlorobenzene (156.17 g, 815.7 mmol)And K2CO3 (225.48 g, 1,631.4 mmol)And copper (3.46 g, 54.4 mmol),Then, dibenzo 18-crown-6 (9.80 g, 27.2 mmol) was added thereto,nitrobenzene (2,700 mL) to 220 DEG C, and the reaction mixture is stirred for 24 hours.When the reaction is terminated, the reaction is filtered through silicagel filterAfter the reaction mixture was quenched with water, the water in the reaction mixture was removed,After filtration under reduced pressure,Dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 127.33 g (yield: 75%) of the product.

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; Duksan Neolux Co.,Ltd.; Yoon Jin-ho; Jeong Ho-yeong; Park Mu-jin; Kim Jeong-seok; Lee Seon-hui; (46 pag.)KR2018/128292; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, molecular formula is C9H11Cl, 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. category: chlorides-buliding-blocks

General procedure: To a solution of 4-phenylbutyl benzoate 1a (127 mg, 0.5 mmol) and N-hydroxyphthalimide (8.16 mg, 0.05 mmol) in CH3CN (1.7 mL) was added cerium(IV) ammonium nitrate (548 mg, 1.0 mmol) at 0 C. The reaction mixture was immediately warmed to room temperature and stirred for 2 h. The mixture was then filtered through a short column of alumina (hexane-EtOAc 1:1), and the filtrate was concentrated. The residue was purified with flash column chromatography (silica gel, hexane-EtOAc 70:1 to 50:1) to provide 4-benzoyloxy-1-phenylbutyl nitrate 2a in 81% yield (128 mg). 1.0 mmol) at 0 C. The reaction mixture was immediately warmed to room temperature and stirred for 2 h. The mixture was then filtered through a short column of alumina (hexane-EtOAc 1:1), and the filtrate was concentrated. The residue was purified with flash column chromatography (silica gel, hexane-EtOAc 70:1 to 50:1) to provide 4-benzoyloxy-1-phenylbutyl nitrate 2a in 81% yield (128 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104-52-9, its application will become more common.

Reference:
Article; Kamijo, Shin; Amaoka, Yuuki; Inoue, Masayuki; Tetrahedron Letters; vol. 52; 36; (2011); p. 4654 – 4657;,
Chloride – Wikipedia,
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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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Chloro-3-methoxyaniline

A stirred solution of 4-chi oro-3-methoxy-aniline (92, 5 g, 31.73 mmol) and diethyl 2- (ethoxymethylene)propanedioate (77, 10.29 g, 47.59 mmol, 9.53 mL) was heated to 100C and stirred for 2 hours and then further heated to 165 C and stirred for an additional hour. Diphenyl ether (50.0 mL) was added to the resulting solution and the reaction was heated to 280 C and stirred for 5 hours. The resulting reaction mixture was cooled to room temperature, pet ether (250 mL) was added and the reaction was stirred for 10 minutes at room temperature. The resulting solid was filtered, washed with pet ether and dried under vacuum to yield ethyl 6-chloro-4- hydroxy-7-methoxy-quinoline-3-carboxylate (93, 8.0 g, 28.40 mmol, 89.51% yield) as an off white solid. LCMS (ES+): m/z 282 [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 13726-14-2.

Reference:
Patent; C4 THERAPEUTICS, INC.; NASVESCHUK, Christopher, G.; HENDERSON, James, A.; VORA, Harit, U.; VEITS, Gesine, Kerstin; PHILIPS, Andrew, J.; (576 pag.)WO2020/51235; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 6276-54-6, 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 6276-54-6 as follows.

[0086] Under stirring, a solution of di-tert-butyl di-carbonate (23.79 g, 110 mmol) in chloroform (50 mL) is slowly addedinto a solution of 3-chloropropylamine hydrochloride (11.0 g, 110 mmol) and triethylamine (18.42 mL, 130 mmol) inchloroform (50 mL). After stirring overnight at room temperature, a brown oil is obtained as a crude product. Thencompound (8-2) (22 g, 95%) as a colorless solid is produced by Kugelrohr distillation at a temperatures of less than 48 C.

According to the analysis of related databases, 6276-54-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangzhou Bensheng Pharmaceutical Co., Ltd.; XU, Rongzhen; XIE, Fuwen; LAI, Hongxi; RONG, Frank; EP2615092; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics