• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】32134

【品名】Methyl 3-hydroxy-2-thiophenecarboxylate

【CA登记号】

【 分 子 式 】C6H6O3S

【 分 子 量 】158.17784

【元素组成】C 45.56% H 3.82% O 30.34% S 20.27%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(I)

The reaction of methyl 3-hydroxythiophene-2-carboxylate (I) with PCl5 in refluxing CCl4 gives 3-chlorothiophene-2-carboxylic acid (II), which by treatment with NaHSO3 and Cu in basic water at 143 C in a pressure vessel is converted into 3-sulfothiophene-2-carboxylic acid (III). The esterification of (III) with refluxing methanol affords methyl 3-sulfothiophene-2-carboxylate (IV), which by reaction with refluxing SOCl2 yields methyl-3-chlorosulfonylthiophene-2-carboxylate (V). The condensation of (V) with sarcosine ethyl ester (VI) in hot CHCl3 gives methyl-3-(N-ethoxycarbonyl-methyl-N-methylsulfamoyl)thiophene-2-carboxylate (VII), which is cyclized by treatment with sodium methoxide in refluxing methanol affording 3-ethoxycarbonyl-4-hydroxy-2-methyl-2H-thieno-[2,3-e]-1,2-thiazine-1,1-dioxide (VIII). Finally, this compound is condensed with 2-aminopyridine (IX) in refluxing toluene.

1 Horomatka, O.; Binder, D.; Pfister, R.; Zeller, P. (F. Hoffmann-La Roche AG); Thienothaiazine derivatives. DE 2537070; FR 2303803; JP 51048694; NL 7510057 .
2 Serradell, M.N.; Blancafort, P.; Castaner, J.; Tenoxicam. Drugs Fut 1982, 7, 7, 493.
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) 32134 Methyl 3-hydroxy-2-thiophenecarboxylate C6H6O3S 详情 详情
(II) 32135 3-Chloro-2-thiophenecarboxylic acid 59337-89-2 C5H3ClO2S 详情 详情
(III) 32136 3-Sulfothiophene-2-carboxylic acid; 3-Sulfo-2-thiophenecarboxylic acid C5H4O5S2 详情 详情
(IV) 32137 Methyl 3-sulfothiophene-2-carboxylate; 2-(Methoxycarbonyl)-3-thiophenesulfonic acid C6H6O5S2 详情 详情
(V) 17836 Methyl 3-(chlorosulfonyl)-2-thiophenecarboxylate; Methyl-3-chlorosulfonylthiophene-2-carboxylate C6H5ClO4S2 详情 详情
(VI) 32138 Sarcosine ethyl ester; Ethyl 2-(methylamino)acetate 52605-49-9 C5H11NO2 详情 详情
(VII) 32139 Methyl-3-(N-ethoxycarbonyl-methyl-N-methylsulfamoyl)thiophene-2-carboxylate; Methyl 3-[[(2-ethoxy-2-oxoethyl)(methyl)amino]sulfonyl]-2-thiophenecarboxylate C11H15NO6S2 详情 详情
(VIII) 32140 Ethyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate; 3-Ethoxycarbonyl-4-hydroxy-2-methyl-2H-thieno-[2,3-e]-1,2-thiazine-1,1-dioxide C10H11NO5S2 详情 详情
(IX) 11305 2-Pyridinamine; 2-Pyridinylamine; 2-Aminopyridine 504-29-0 C5H6N2 详情 详情
Extended Information