Tag: M.W=200-300

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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H6BrCl

EXAMPLE 10; (5-{2-r5-(S-Chloro-2-methylphenvl)hexahvdropyrrolor3.4-clpyrrol-2piH)-vn-13-thiazol-5-vU- 2H-tetrazol-2-yl)acetic acid; Step 1 tert-Butgamma\ 5-(5-chloro-2-methvlphenvpihexahgammadropyrrolo[3,4-clpyrrole-2(lH)- carboxylate; Into a 50 mL flask equipped a magnetic stir bar and a rubber septum was added tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(lH)-carboxylate oxalate (2 00 g, 6 62 mmol),10 palladium(II) acetate (149 mg, 0 66 mmol), racemic-B INAP (824 mg, 1 32 mmol) and sodium tert-butoxide (1 91 g, 19 9 mmol) The vial was evacuated under vacuum (10 mm Hg) and backfilled with N2 (repeated 3 times) Toluene (14 mL) and 2-bromo-4-chlorotoluene (2 18 g, 10 6 mmol) were added to the flask and the solvent was degassed for 10 mm with a steady flow of nitrogen before being heated to 115 0C for 20 h The reaction mixture was partitioned between15 EtOAc (200 mL) and water (150 mL) The aqueous layer was extracted with EtOAc (5 x 50 mL) and the combined organic layers were washed with brine, dried over Na?Spsi4 and concentrated The resulting pale brown oil was purified by column chromatography on silica gel, elutmg with 0percent EtOAc m hexanes to 40percent EtOAc m hexanes as a gradient The desired product was obtained as a yellow oil

The synthetic route of 27139-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; LACHANCE, Nicolas; LEGER, Serge; OBALLA, Renata, M.; POWELL, David; TRANMER, Geoffrey, K.; MARTINS, Evelyn; GAREAU, Yves; WO2010/108268; (2010); A1;,
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Electric Literature of 329944-72-1, The chemical industry reduces the impact on the environment during synthesis 329944-72-1, name is 3-Bromo-5-chlorotoluene, I believe this compound will play a more active role in future production and life.

Azobisisobutyronitrile (AIBN, 1.0 g, 6.05 mmol) was added to a stirred solution of 1-bromo-3-chloro-5-methylbenzene (25 g, 121 mmol) in CCl4 (250 mL). The reaction mixture was then cooled to 0 C and N-bromosuccinimide (21.65 gm, 121 mmol) was added and the reaction mixture was refluxed for 3 hours. The reaction mixture was cooled to room temperature and the solid was removed by filtration. The filtrate was concentrated to give the title compound as brown liquid (25 g), which was taken to the next step without further purification.

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, 3-Bromo-5-chlorotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cortendo AB; Blass, B. E.; Abou-Gharbia, M. A.; Childers, W. E.; Iyer, P.; Boruwa, J.; (143 pag.)CN105722823; (2016); A;,
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Electric Literature of 6579-54-0,Some common heterocyclic compound, 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, molecular formula is C6H3Cl3O2S, 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 mixture of corresponding 7 (150mg, 0.4mmol) in anhydrous THF (15mL) and DMF(3mL), corresponding sulfonyl chloride (0.5mmol) was added slowly at 0C and stirred at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate (50mL×3). The combined organic layer was washed by saturated sodium chloride solution (40mL×3) and concentrated. The residue was purified by silica gel chromatography to afford 8a-8i.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dichlorobenzenesulfonyl chloride, its application will become more common.

Reference:
Article; Zhang, Li; Zhang, Beichen; Zhao, Jingyun; Zhi, Yanle; Wang, Lu; Lu, Tao; Chen, Yadong; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 942 – 951;,
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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. 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, A new synthetic method of this compound is introduced below., Recommanded Product: 13745-86-3

A 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of 11-chlorodibenzo [b,fj[l,4]thiazepine in toluene 350 cc [52 gm (0.22 moles)], and was added 73.0 gm (0.84 moles) of piperazine at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 70C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC. The reaction mixture was cooled to at 20C to 25C and was added 250 cc DM water and was stirred for 30 min. at 25-30C. The layers were separated and the organic layer washed with 250 cc DM water. The organic layer was forwarded for the next step. Purity of 11- piperazinyldibenzo [b,fj-[l,4] -thiazepine in toluene was more than 97% (area % by HPLC).Example 5. ll-piperazinyldibenzo[b,fl[l,41 thiazepineA 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of l l-chlorodibenzo[b,fj[l,4] thiazepine in toluene [52 gm (0.22 moles)], and was added 73.0 gm (0.84 moles) of piperazine at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 700C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of Formula III). The reaction mixture was cooled to at 20C to 25C was added 250 cc DM water and was stirred for 30 min. at 25-30C. The layers were separated and the organic layer washed with 250 cc DM water. To the organic phase was added 250 cc water and was acidified with formic acid to obtain a pH of 2-3. The contents were stirred for 15 min. and the layers were separated. The aqueous layer was washed with 150 cc toluene and the aqueous layer was basified with sodium carbonate to a pH of 8 to 10 and extracted with 3x 250 cc of toluene. Combine the organic layer and washed with DM water 130 cc twice. Purity of 1 l-piperazinyldibenzo[b,f][l,4] thiazepine in toluene was more than 99 % (area % by HPLC). Example 6. 11- piperazinyldibenzo fb,f|-[l.,41 -thiazepineA 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of 11-chlorodibenzo [b,fj[l,4] -thiazepine in toluene [52 gm (0.22 moles)], and the mixture was stirred for 15 min 45-50C.The resulting solution was added piperazine 73.0 gm (0.84 moles) at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 7O0C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of Formula III). The reaction mixture was cooled to 20C to 25C, to which, was added 250 cc DM water and was stirred for 30 min. at 25-300C. The layers were separated and the organic layer washed with 250 cc DM water. To the organic phase was added 250 cc water and it was acidified with acetic acid to obtain a pH of 2-3. The contents were stirred for 15 min. and layers were separated. The aqueous layer was washed with 150 cc toluene and the aqueous layer was basified with sodium carbonate to a pH of 8 to 10 and extracted with 3x 250 cc of toluene. Combine the organic layer and washed with DM water 130 cc twice. Purity of 11- piperazinyldibenzo [b,fj-[l,4] -thiazepine in toluene was more than 99 % (area % by HPLC); A 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of l l-chlorodibenzo[b,f][l,4] thiazepine in toluene [52 gm (0.22 moles)], and the mixture was stirred for 15 min 45-50C. To the resulting solution was added piperazine 73.0 (0.84 moles) at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 70C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of formula III) and was cooled to 20C to 25C. The reaction mixture was added 250 cc DM water and was stirred for 30 min. at 25-30C. The layers were separated and the organic layer washed with 250 cc DM water. The organic phase was distilled off under vacuum below 70C. Traces of toluene were removed by adding n-butanol. To the resultant oily mass was added 150 cc n-butanol. The mixture was stirred for 24 hrs and chilled to 0-5C. The reaction mass was filtered with the filtrate (mother liquor) containing 11-piperazinyldibenzo [b,fj [l,4]thiazepine. Purity of 11- piperazinyldibenzo[b,fj [1,4] thiazepine in toluene was more than 98.0% (area % by HPLC).Example 9. llpiperazinyldibenzo[b,fl [1,41 thiazepineA 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of 11 -chlorodibenzo [b,f][ 1,4] thiazepine in toluene [52 gm (0.22 moles)], and the mixture was stirred for 15 min 45-50C. To the resulting solution was added piperazine 73.0 gm (0.84 moles) at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 7O0C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC and was cooled to 20C to 25C. To the reaction mixture was added 250…

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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2008/121415; (2008); A2;,
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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 27139-97-5 as follows. Computed Properties of C7H6BrCl

A 12 mL vial equipped with a magnetic stir bar was charged with 2-bromo-4-chloro methylbenzene (357.3 mg, 1.74 mmol). To this vial was added phenyl boronic acid (233 mg, 1.91 mmol), Pd(OAc)2 (19.5 mg, 0.09 mmol), P(Ph)3 (91.2 mg, 0.35 mmol), and K2 C03 (480 mg, 3.58 mmol). The vial was flushed with nitrogen and evacuated 3 times. A 10:1 mixture of anhydrous THF:H20 was then added by syringe. The resulting mixture was heated at 80 °C for 18 hours. The reaction was then cooled to rt whereupon 5 mL HzO was added. The reaction was extracted with EtOAc (3 x 10 mL) and the combined organic layers were dried over Na2 S04, filtered and concentrated under reduced pressure to yield an oil. The oil was purified using a 12 g ISCO Si02 column eluting with pure hexanes over a 30 minute period. The desired fractions were combinedand concentrated under reduced pressure to yield 5-chloro-2-methyl-1,1′-biphenyl as a clear oil(332 mg, 94percent yield). 1H NMR (400 MHz, Chloroform-d) 8 7.37-7.30 (m, 2H), 7.30-7.24 (m,1H), 7.23-7.18 (m, 2H), 7.16-7.09 (m, 3H), 2.14 (s, 3H).

According to the analysis of related databases, 27139-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; JONES, Todd, K.; CISAR, Justin, S.; GRICE, Cheryl, A.; WANG, Dong-Hui; WEBER, Olivia, D.; WO2015/3002; (2015); A1;,
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Electric Literature of 1127-85-1, These common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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.

Reference Example 39 (S)-1-(2-chloro-5,6,7,8-tetrahydroquinazolin-4-yl)-N-methylpiperidine-3-carboxamide Diisopropylethylamine (3.4 ml, 19.7 mmol) was added into chloroform (25 ml) solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (1 g, 4.92 mmol) prepared in Reference Example 33 and (R)-(-)-3-piperidinecarboxylic acid (0.7 g, 5.42 mmol), and then they were stirred at 60 C. for 2 days. After cooling the reaction solution to room temperature, methylamine hydrochloride (0.33 g, 4.92 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.94 g, 4.92 mmol) and 1-hydroxybenzotriazole hydrate (0.67 g, 4.92 mmol) were added thereto, they were stirred at room temperature overnight. The reaction solution was diluted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was crystallized by using ether/ethyl acetate to give the titled compound (436 mg) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 6.22 (m, 1H), 3.93 (m, 1H), 3.74 (m, 1H), 3.34 (m, 1H), 3.10 (m, 1H), 2.81 (m, 4H), 2.49 (m, 3H), 1.93-1.84 (m, 4H), 1.70-1.60 (m, 4H).

The synthetic route of 1127-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; SIM, Jae Young; CHA, Myung; KIM, Tae Kyun; YOON, Young Ae; KIM, Dong Hoon; (59 pag.)US2016/90374; (2016); A1;,
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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. 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H2ClF3O2S

General procedure: A solution of compound 8 (90 mg, 0.44 mmol), 4-chlorobenzenesulfonyl chloride (103 mg, 0.49 mmol) and triethylamine (68 muL, 0.49 mmol) in dichloromethane (5 mL) was stirred at room temperature for 18 h. The reaction was quenched through the addition of water (20 mL) and the pH adjusted to pH 6-7 using aqueous phosphate buffer solution (0.5 M, pH 7). The mixture was then diluted with dichloromethane (20 mL) and the separated aqueous layer further extracted with dichloromethane (2 x 20 mL). The combined organic layers were washed with aqueous phosphate buffer solution (0.5 M, pH 7) (20 mL), dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. Purification by flash chromatography (dichloromethane/methanol, 40:1) afforded compound 9a as a beige solid (96 mg, 0.25 mmol, 56%).

According to the analysis of related databases, 220227-21-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brimble, Margaret A.; Cook, Gregory M.; Davison, Emma K.; Ferguson, Scott A.; Harbison-Price, Nichaela; Harper, Andrew D.; Heikal, Adam; Jeong, Joo Young; Knottenbelt, Melanie K.; Krittaphol, Woravimol; McConnell, Michelle A.; McGowan, John E.; Mros, Sonya; Rennison, David; Van Zuylen, Essie M.; Walker, Greg F.; Bioorganic and medicinal chemistry letters; (2020);,
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Application of 220227-21-4, 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. 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 1,3-dihydro-2H-imidazol-2-one (10,12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil,17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL),dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac).

The chemical industry reduces the impact on the environment during synthesis 2,4,5-Trifluorobenzene-1-sulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Sittihan, Satapanawat; Jumpathong, Watthanachai; Sopha, Pattarawut; Ruchirawat, Somsak; Bioorganic and Medicinal Chemistry Letters; vol. 30; 1; (2020);,
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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. 14862-52-3, name is 3,5-Dibromochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 3,5-Dibromochlorobenzene

Vapor phase chlorination step: A reactor equipped with a lateral reaction tube (diameter of 4 cm, length of 50 cm), a vaporizer and a preheating tube which are capabe of outward temperature control, was used and 1 mol of chlorine gas preheated at 300 C. was fed into the reaction tube and a solution of 1 mol of 1-chloro-3,5-dibromobenzene in 5 mol of carbon tetrachloride was preheated at 300 C. to vaporize it and the vapor was fed into the reaction tube during 50 minutes to react them at 340 C. The residence time of the reaction mixture was about 50 seconds. The discharged gas from the reaction tube was fed into an alkaline aqueous solution of sodium thiosulfate to collect the reaction product. The phase separation was carried out at room temperature and carbon tetrachloride was distilled off to obtain oily product. The oily product was distilled to obtain 165 g. of 1,3,5-trichlorobenzene in yield of 91%.

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US4368340; (1983); A;,
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Reference of 61881-19-4, 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 61881-19-4 as follows.

General procedure: Add sodium acetate, trifluoroethylimidyl chloride (II), hydrazone (III), and 1 mL of organic solvent to the 35 mL Schlenk tube according to the raw material ratio in Table 1.Mix and stir well. After the reaction is completed according to the reaction conditions in Table 2, 2-4 hours,Add elemental iodine, continue the reaction for 1-2 hours, filter, and stir the sample in silica gel.After purification by column chromatography, the corresponding 5-trifluoromethyl-substituted 1,2,4-triazole compound (I) is obtained. The reaction process is shown by the following formula:

According to the analysis of related databases, 61881-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Sci-Tech University; Chen Zhengkai; Hu Sipei; Yang Zuguang; (10 pag.)CN110467579; (2019); A;,
Chloride – Wikipedia,
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