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【结 构 式】

【分子编号】21238

【品名】4-(methylsulfanyl)benzoyl chloride

【CA登记号】

【 分 子 式 】C8H7ClOS

【 分 子 量 】186.66168

【元素组成】C 51.48% H 3.78% Cl 18.99% O 8.57% S 17.18%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(II)

The reaction of 4-(methylthio)benzoic acid (I) with SOCl2 in refluxing benzene gives 4-(methylthio)benzoyl chloride (II), which is then condensed with 1,3-dihydro-4-methyl-2H-imidazol-2-one (III) by means of AlCl3 in hot nitrobenzene.

1 Dage, R.C.; Schnettler, R.A.; Grisar, J.M. (Aventis Pharmaceuticals, Inc.); 4-Aroylimidazol-2-ones. BE 0883856; DE 3021792; FR 2459233; GB 2055364; JP 56005463 .
2 Pento, J.T.; Serradell, M.N.; Castaner, J.; Blancafort, P.; RMI-17,043. Drugs Fut 1983, 8, 4, 343.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 30683 4-(methylsulfanyl)benzoic acid 13205-48-6 C8H8O2S 详情 详情
(II) 21238 4-(methylsulfanyl)benzoyl chloride C8H7ClOS 详情 详情
(III) 30684 4-methyl-1,3-dihydro-2H-imidazol-2-one C4H6N2O 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

The acylation of 2,3-dihydrobenzofuran (I) with acetyl chloride and AlCl3 in dichloromethane gives 5-acetyl-2,3-dihydrobenzofuran (II), which by reaction with sulfur, morpholine (III) and p-toluenesulfonic acid at high temperature yields 2-(2,3-dihydrobenzofuran-5-yl)thioacetic acid morpholide (IV). The hydrolysis of (IV) with H2SO4 in refluxing water-acetic acid affords 2-(2,3-dihydrobenzofuran-5-yl) acetic acid (V), which is esterified to (VI) with ethanol and H2SO4 in refluxing toluene. The condensation of the ester (VI) with 4-(methylthio)benzoyl chloride (VII) by means of SnCl4 in refluxing dichloromethane gives ethyl 2-[7-[4-(methylthio)benzoyl]benzofuran-5-yl]acetate (VIII), which by hydrolysis with NaOH in refluxing methanol-water yields the corresponding acid (IX). Finally, this compound is dehydrogenated with N-bromosuccinimide (NBS) and dibenzoyl peroxide in refluxing CCl4.

1 Dunn, J.P. [Syntex (Syntex (USA) LLC); Aroyl benzofuran and benzothiophene acetic and propionic acids, processes for their production and pharmaceutical compositions containing them. AU 8430593; EP 0132130; ES 8604554; ES 8607960; JP 85038376 .
2 Prous, J.; Castaner, J.; TIFURAC SODIUM < Rec INNM; USAN >. Drugs Fut 1989, 14, 8, 775.
3 Tomolonis, A.J.; Dunn, J.P.; Ackerman, N.A.; Analgetic and antiinflammatory 7-aroylbenzofuran-5-yl acetic acids and 7-aroylbenzothiophene-5-ylacetic acids. J Med Chem 1986, 29, 11, 2326.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 14499 2,3-Dihydrobenzofuran; 2,3-dihydro-1-benzofuran 496-16-2 C8H8O 详情 详情
(II) 21233 1-(2,3-dihydro-1-benzofuran-5-yl)-1-ethanone 90843-31-5 C10H10O2 详情 详情
(III) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(IV) 21235 2-(2,3-dihydro-1-benzofuran-5-yl)-1-(4-morpholinyl)-1-ethanethione C14H17NO2S 详情 详情
(V) 14500 2-(2,3-dihydro-1-benzofuran-5-yl)acetic acid 69999-16-2 C10H10O3 详情 详情
(VI) 21237 ethyl 2-(2,3-dihydro-1-benzofuran-5-yl)acetate C12H14O3 详情 详情
(VII) 21238 4-(methylsulfanyl)benzoyl chloride C8H7ClOS 详情 详情
(VIII) 21239 ethyl 2-[7-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1-benzofuran-5-yl]acetate C20H20O4S 详情 详情
(IX) 21240 2-[7-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1-benzofuran-5-yl]acetic acid C18H16O4S 详情 详情
Extended Information