Ethanol → Ethyl 1H-benzimidazole-6-carboxylate

HRID 465038

반응식

HRID 465038 반응식
Cl.[C:2]([C:5]1[CH:13]=[CH:12][C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH:6]=1)([OH:4])=[O:3].[CH2:14](O)[CH3:15]>S(=O)(=O)(O)O>[CH2:14]([O:3][C:2]([C:5]1[CH:13]=[CH:12][C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH:6]=1)=[O:4])[CH3:15]

참가 물질

4

반응물 2

HCID 702EthanolHCID 17368244Benzodiazole-5-carboxylic acid HCl

생성물 1

HCID 13505555Ethyl 1H-benzimidazole-6-carboxylate

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

According to a method similar to that described in Zhur. Obschei Khim., vol. 32, pp 835-41 (1953), 3,4-diaminobenzoic acid was prepared. A formic acid solution (200 ml) of 3,4-diaminobenzoic acid (8 g) thus prepared was refluxed for 4 hrs to yield 5-carboxybenzimidazole.hydrochloride (8.9 g). The carboxylic acid (8.9 g) was refluxed with heating for 3.5 hrs in a mixture of sulfuric acid (4 ml) and absolute ethanol (140 ml) to yield 5-ethoxycarbonylbenzimidazole (mp. 93°-94° C., 7.8 g). An anhydrous tetrahydrofuran solution (20 ml) of the ester (7.5 g) was added to an anhydrous tetrahydrofuran suspension (50 ml) of lithium aluminium hydride (6.5 g) while cooling. The mixture was stirred for 3 hrs at room temperature to yield 5-hydroxymethylbenzimidazole (mp. 128.4° C., 3.62 g). A 47% aqueous hydrobromic acid solution (33 ml) containing the benzimidazole derivative (2.2 g) and cysteamine hydrochloride (1.9 g) was refluxed with heating for 7 hrs to yield 5-[(2-aminoethyl)thiomethyl]benzimidazole.2 hydrobromide (mp. 224°-225° C., 4.2 g).

출처 및 근거

ORD 기록
ord-d7471582180a49399b42ee5b3fa402cf
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04550118

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