Tag: M.W=100-200

These common heterocyclic compound, 1939-99-7, name is Phenylmethanesulfonyl chloride, 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. Application In Synthesis of Phenylmethanesulfonyl chloride

K2CO3 (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 (100mL) 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 Na2SO4, 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 N-(2-bromoethyl)(phenyl)methanesulfonamide (7.0 g, 80%) as a pale yellow solid. 1H NMR (300 MHz, CDCl3) 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.

The synthetic route of Phenylmethanesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; RENE, Olivier; (86 pag.)WO2017/102796; (2017); A1;,
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Reference of 1435-48-9, 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. 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 60% sodium hydride (2.00 g) in DMF (25 mL) was added dropwise a solution of tert-butyl4-(hydroxymethyl)piperidine-1-carboxylate (8.00 g) in DMF (25 mL) at 0C, and then 2,4-dichloro-1-fluorobenzene (4.38mL) was added thereto. The reaction mixture was stirred at room temperature for 18 hr. To the reaction mixture wereadded water and aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organiclayer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reducedpressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give tert-butyl 4-((2,4-dichlorophenoxy)methyl)piperidine-1-carboxylate as a crude product.

The chemical industry reduces the impact on the environment during synthesis 2,4-Dichloro-1-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Pharmaceutical Company Limited; IKEDA, Shuhei; KOIKE, Tatsuki; AIDA, Jumpei; FUSHIMI, Makoto; KUSUMOTO, Tomokazu; SUGIYAMA, Hideyuki; MIYAZAKI, Masako; TOKUHARA, Hidekazu; HATTORI, Yasushi; KAMATA, Makoto; (149 pag.)EP3279191; (2018); A1;,
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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. 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

Synthesis of2-chloro-8-(l-phenylethyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0454] 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 (2 mL) under argon atmosphere was added sodium hydride (27 mg, 1.16 mmol) at 0 C. After stirring for 10 mins, (1-bromoethyl) benzene (130 mg, 0.70 mmol) was added to the reaction mixture at 0 C and stirred for 1 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with 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-(l-phenylethyl)-7, 8-dihydro- 6H-pyrimido [5, 4-b] [1, 4] oxazine (140 mg, 87%) as an off-white solid. 1H-NMR (CD3OD, 400 MHz): delta 7.60 (s, 1H), 7.39-7.23 (m, 5H), 6.20-6.11 (m, 1H), 4.18-4.10 (m, 1H), 3.98- 3.91 (m, 1H), 3.50-3.41 (m, 1H), 3.10-3.02 (m, 1H), 1.60 (s, 3H); LCMS: 275.8 (M+l); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.70 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,
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Adding a certain compound to certain chemical reactions, such as: 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, 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 106131-61-7, Application In Synthesis of 3,6-Dichloro-1,2,4,5-tetrazine

General procedure: In a 100 mL round bottom flask, was introduced the diol(0.33 mmol), s-collidine (0.39 mmol) and 20 mL of dry dichloromethane and the mixture was stirred at room temperature. 3,6-dichloro-s-tetrazine 1 (0.66 mmol) was dissolved in dry dichloromethane and added dropwise in the flask. After2 h the reaction is complete (TLC) and the solvent removed under reduced pressure. The crude residue was purified by column chromatography on silica gel (eluent petroleumether/ethyl acetate 1/1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,6-Dichloro-1,2,4,5-tetrazine, and friends who are interested can also refer to it.

Reference:
Article; Guermazi, Refka; Royer, Lorna; Galmiche, Laurent; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Journal of Fluorescence; vol. 26; 4; (2016); p. 1349 – 1356;,
Chloride – Wikipedia,
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Electric Literature of 33786-89-9, These common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, 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 6 In an autoclave, 28.6 g. of 3,5-diaminochlorobenzene, 2 g. of cuprous chloride and 122 g. of 28% ammonia water were charged to react them at 165 to 170 C. for 8 hours to obtain 1,3,5-triaminobenzene. Ammonia was discharged and the product was recrystallized to obtain 19 g. of 1,3,5-triaminobenzene.

The synthetic route of 33786-89-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US4380670; (1983); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 102-49-8, A common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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: A mixture of acid 6 (0.5 g, 1 mmol), EDCI (0.21 g, 1.1 mmol), and HOBt (0.15 g, 1 mmol) in dry CH3CN (10 mL) was stirred at room temperature for 30 min and then treated with the benzyl amine 7a (0.11 mL, 1 mmol). The mixture was stirred at room temperature for an additional 24 h. Then the solution was evaporated to dryness in vacuum. The residue was dissolved in ethyl acetate (20 mL) and washed sequentially with brine (2 .x. 5 mL), 10percent aqueous sodium carbonate (2 .x. 5 mL), 10percent aqueous citric acid (2 .x. 5 mL), and water (2 .x. 5 mL). The organic layer was dried over anhydrous sodium sulfate. Concentration of the dried extract yielded an oily residue, which was crystallized (CH2Cl2/n-C6H14) to give pure 8a amide in 27percent yield.

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fallah-Tafti, Asal; Foroumadi, Alireza; Tiwari, Rakesh; Shirazi, Amir Nasrolahi; Hangauer, David G.; Bu, Yahao; Akbarzadeh, Tahmineh; Parang, Keykavous; Shafiee, Abbas; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 4853 – 4858;,
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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 39226-95-4 as follows. SDS of cas: 39226-95-4

General procedure: Amine (0.386 mL) was added to Triton-B and stirred for 10 min followed by the addition of CS2 (0.321 mL) dropwise. Then dimethyl acetate carboxylate was added again dropwise. The mixture was stirred for 2.5 h. TLC plate showed the formation of some new compound. The reaction was seen continuously and formation of product was monitored with TLC. After the completion, the reaction mixture was drained into distilled water and extraction was done three times using ethyl acetate (Scheme-I)

According to the analysis of related databases, 39226-95-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Srivastava, Nitin; Saxena; Asian Journal of Chemistry; vol. 31; 1; (2019); p. 176 – 180;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 6775-78-6, A common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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.

6-Chloroimidazo[l,2-b]pyridazine (4.95 g, 31.6 mmol) [purchased from Combi-Blocks] was dissolved in 60 mL concentrated sulfuric acid, cooled in an ice bath, and nitric acid (9.9 mL, 158 mmol) was added dropwise while stirring. The reaction was stirred at 0 0C for 30 minutes, then at ambient temperature for 4.5 hours to reach completion. The reaction was poured onto ice, and the resulting aqueous mixture was neutralized with 50% NaOH aqueous solution and then extracted with EtOAc (3 x 400 mL). The organic layers were combined and washed with water (2 x 400 mL) and brine (400 mL), dried (Na2SO4), filtered and concentrated to yield the product as a yellowish powder (5.7 g, 91% yield).

The synthetic route of 6775-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; ANDREWS, Steven, W.; HAAS, Julia; JIANG, Yutong; ZHANG, Gan; WO2010/33941; (2010); 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. 348-59-4, name is 2,5-Dichlorofluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3Cl2F

(Step 1) Synthesis of 1,4-dichloro-2-fluoro-5-nitrobenzene (0422) According to (Step 1) of Example 19, 1,4-dichloro-2-fluorobenzene (1.00 g) was dissolved instead of 1-chloro-2-fluoro-4-methylbenzene in TFA (10 mL). To the solution, fuming nitric acid (5.0 mL) was added dropwise. The mixture was stirred at room temperature for 3 hours, and then, the solution was added to an aqueous sodium bicarbonate solution. The precipitated solid was collected by filtration and dried to obtain 1.30 g of the title compound as a white 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 348-59-4.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; KAWAI, Yuichi; IRIE, Hiroki; SAGARA, Takeshi; MIYADERA, Kazutaka; (63 pag.)US2017/217970; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

39226-95-4, name is 2,3-Dichlorobenzylamine, 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: 2,3-Dichlorobenzylamine

General procedure: The chiral monomer (R)-2-(2,4-bis(benzyloxy)-5-chlorobenzoyl)-1, 2,3,4-tetrahydroisoquinoline-3-carboxylic acid 9 (100 mg, 0.19 mmol), EDCI (43.7 mg, 0.228 mmol), HOBt (30.8 mg, 0.228 mmol) and 2-chloro benzylamine (0.15 mL, 1.2 mmol) in DMF (3 mL) was stirred overnight at room temperature. The organic layer was washed successively with 2 M HCl and 2 M NaOH, then dried over anhydrous/Na2SO4, filtered and evaporated under vacuum to afford a yellowish powder that was used for the next step reaction without further purification. To the anhydrous CH2Cl2 (3 mL) solution of this product cooled to 0 C under N2 was added BCl3 (1.0 M in CH2Cl2, 0.57 mL, 0.56 mmol). The reaction mixture was allowed to warm to RT and stirred for 1.5 h. Sat. NaHCO3 solution (5 mL) was added and CH2Cl2 was removed under vacuum. The aqueous residue was extracted with EtOAc (4 x 10 mL) and evaporated under vacuum to produce a brown powder. The powder was purified by column chromatography over silica gel eluted with CH2Cl2-MeOH (30: 1, v/v) to give compound 10 (82.8 mg) as a white powder, yield: 91%.

The synthetic route of 39226-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Chuanpeng; Wu, Xingkang; Li, Zhenyu; Zhu, Jing; Lu, Chunhua; Shen, Yuemao; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 85 – 96;,
Chloride – Wikipedia,
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