Potassium Carbonate → Benzimidazole

HRID 2351302Notes

Reaction equation

Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.BrCC(C1C(C)=C(SCC)C=CN=1)=O.C([O-])([O-])=O.[K+].[K+]>>[N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][CH:2]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 785722-Chlorobenzimidazole

HCID 144215532-Bromoacetyl-4-ethylthio-3-methylpyridine

Product 1

HCID 5798Benzimidazole

Procedure

2-Chlorobenzimidazole is reacted with 2-bromoacetyl-4-ethylthio-3-methylpyridine in the presence of K2CO3 to give 2-chloro-1-[2-[4-ethylthio-3-methylpyridyl])-2-oxoethyl]benzimidazole. This is reacted with thiourea and treated with NH4OH to give 2-mercapto-1-(2-(2-(4-ethylthio-3-methylpyridyl))-2-oxoethyl)benzimidazole. Reduction of this product using NaBH4 gives 1-[2-hydroxy-2-(4-ethylthio-3-methylpyrid-2-yl)ethyl]-2-mercaptobenzimidazole.

Sources & evidence

ORD record: ord-7f981be76bdd4f5ab91db36ab0fe990e
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04873237

Reaction notes

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