Category: chlorides-buliding-blocks

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. 699-89-8, name is 4,7-Dichlorothieno[2,3-d]pyridazine, A new synthetic method of this compound is introduced below., Computed Properties of C6H2Cl2N2S

A 250 mL, round-bottomed flask was equipped with a stir bar and reflux condenser. To the flask was added the product of step 4 (7.65 g, 37.3 mmol), 4-chloroaniline (4.76, 37.3 mmol) in EtOH (75 mL). The mixture was refluxed for 3 h. An orange solid precipitated from the reaction after 3 h. The reaction was cooled to rt and the solid was collected by filtration and washed with hexane. The desired 7-chloro-4-(4-chlorophenylamino)thieno[2,3-d]pyridazine was obtained (6.5 g, 21.9 mmol; 60% yield); mp= 139-142 C; ES MS (M+H)+= 297; TLC (Hexane- EtOAc, 60:40); Rf = 0.48.; To the dichloride from Example 8, step 4 (1.00 g, 4.90 mmol) was added p-chloroaniline (622 mg, 4.90 mmol) and absolute ethyl alcohol (10.0 mL). The mixture was refluxed at 95 C for 2 hrs and then cooled to room temperature. The yellow precipitate (2) that formed was filtered and washed with isopropyl alcohol, 4.0 N KOH, H2O, and then hexane. The filtrate (2) was then mixed 6-aminobenzothiazole (883 mg, 5.88 mmol) in 10 mL of n-butanol, and heated at 150 C overnight. The reaction was allowed to cool to room temperature before the solvent was removed by rotary evaporation. The residue was treated sequentially with aqueous 4.0 N KOH solution and extracted with dichloromethane (50 mL), dried (MgSO4), and the solvent evaporated. The crude product was purified by flash chromatography on silica gel using 95% dichloromethane/methanol as the eluent. The structure of the pure title compound was confirmed by LC/MS and NMR: TLC (30% EtOAc/Hexanes) Rf (3) = 0.20; 1H NMR (DMSO) delta 7.2 (dd, 3H), 7.38 (dd, 3H), 7.65 (d, 1H), 8.0 (d, 1H), 8.45 (d, 1H), 8.8 (s, 1H); LC/MS m/z 410 rt = 4.21 min.; Equal equivalents of dichloride (1) and M-NH2 are refluxed in the appropriate amount of absolute ethanol at 95 C for 2 hrs. The reaction mixture is allowed to cool to room temperature and the precipitate (2) that forms is filtered and washed sequentially with isopropyl alcohol, 4.0 N KOH, H2O, and hexane, and then dried. The filtrate (2) is then reacted with 1.2 equivalent of Q-NH2 in an appropriate amount of n-butyl alcohol at 150 C for 10 hrs. The reaction is cooled to room temperature before the solvent is evaporated under reduced pressure. The residue is treated with aqueous 4.0 N KOH solution and extracted with dichloromethane. The organic layer is dried (MgSO4) and evaporated. The crude product (3) is purified by preparative thin layer chromatography (TLC) or flash chromatography on silica gel using dichloromethane/methanol (95:5) as the eluent. Final product is confirmed by LC/MS and/or NMR. The invention compounds of Examples 23 – 25, 48, and 76-80 as shown in the below table were prepared by method A-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; BAYER CORPORATION; EP1228063; (2009); B1;,
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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;,
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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;,
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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;,
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Related Products of 220227-21-4,Some common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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.

Intermediate 19 1,1 -dimethylethyl (2S,4R)-2-methyl-4-{[(2,4,5-trifluorophenyl)sulfonyl]amino}-1- pyrrolidinecarboxylateTo 1 ,1-dimethylethyl (2S,4R)-4-amino-2-methyl-1-pyrrolidinecarboxylate (0.075 g, 0.38 mmol) in DCM (~5 mL) was added a solution of 2,4,5-trifluorobenzenesulfonyl chloride (0.075 g, 0.38 mmol) in DCM (~5 mL) and DIPEA (0.13 mL, 0.75 mmol). The resultant mixture was stirred at room temperature overnight, evaporated and loaded onto a 5 g silica SPE cartridge, eluting sequentially with DCM and ethyl acetate. The ethyl acetate fractions were combined and evaporated to afford the title compound (0.0942 g). LC-MS: m/z, 395 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,5-Trifluorobenzene-1-sulfonyl chloride, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/26197; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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. category: chlorides-buliding-blocks

In a three-necked flask equipped with a magnetic stirrer and placed under a nitrogen atmosphere, tert-butyl (R)-2-formylpiperidine-1-carboxylate (3.7 g, 17.3 mmol) is dissolved in tetrahydrofuran (50 mL). (3-Chloro-5-fluorophenyl) bromide (0.5 M solution in THF) (41.6 mL, 20.8 mmol) is added dropwise at -70 C. The mixture is stirred at -70 C. for 5 hours and then hydrolyzed by addition of water at 0 C. The medium is diluted with EtOAc, washed with water and with saturated NaCl solution and then dried over MgSO4 and concentrated by evaporation under reduced pressure (RP). The residue is purified by chromatography on silica gel eluted with a 6/2 cyclohexane/EtOAc mixture. 1.28 g of tert-butyl (2R)-2-[(S)-(3-chloro-5-fluorophenyl)(hydroxy)methyl]piperidine-1-carboxylate are thus obtained in the form of an oil that crystallizes, and 1.27 g of tert-butyl (2R)-2-[(R)-(3-chloro-5-fluorophenyl)(hydroxy)methyl]piperidine-1-carboxylate are obtained in the form of an oil that crystallizes. tert-Butyl (2R)-2-[(S)-(3-chloro-5-fluorophenyl)(hydroxy)methyl]piperidine-1-carboxylate: (M+Na)+=366; [alpha]D20 C.=+16.4+-0.6 (MeOH) and tert-butyl (2R)-2-[(R)-(3-chloro-5-fluorophenyl)(hydroxy)methyl]piperidine-1-carboxylate: (M+Na)+=366; [alpha]D20 C.=-46.1+-0.9 (MeOH)

The synthetic route of 33863-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2010/298377; (2010); 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,
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. 2268-05-5, name is 2,6-Dichlorofluorobenzene, A new synthetic method of this compound is introduced below., Safety of 2,6-Dichlorofluorobenzene

To 2,2,6,6-tetramethylpiperidine (20.07 ml_, 1 18 mmol) dissolved in Tetrahydrofuran (THF) (300 ml.) at 0 0C was added nBuLi (73.9 ml_, 118 mmol) dropwise. The solution was stirred at 0 0C for 10 minutes and cooled to -78 0C. 1 ,3- dichloro-2-fluorobenzene (15 g, 91 mmol, commercially available from e.g. Sigma- Aldrich, Apollo or Alfa Aesar) dissolved in Tetrahydrofuran (THF) (30 ml.) was added dropwise and the solution was stirred at -78 0C for 1 hour. The solution was poured on to dry ice (xs) that had been previously washed with tetrahydrofuran (3 x 100 ml.) and stirred to room temperature over 3 hours. Solvents were removed in vacuo to afford a white solid. The solid was combined with solid isolated from method a) and partitioned between ethyl acetate (200 ml.) and 2N Hydrochloric acid. The aqueous solution was extracted with ethyl acetate (3 x 100 ml_); the combined extracts were washed with brine (50 ml.) and concentrated to a crude solid. The crude solid was recrystalised from cyclohexane/toluene to afford the product 19.03 g. LC/MS = 207/209 (M-H)-, retention time = 0.90 minutes (2 minute method).

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; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics