Imidazole → 3-(1H-imidazol-1-yl)propanoic acid

Participants

Reaction Steps

A mixture of 12.9 g of p-chlorophenol, 36.6 g of 1-bromo-2-(2,6-dichlorophenylthio)-3-(1-imidazolyl)propane [obtainable by reaction of 3-bromopropionic acid with imidazole to give 3-(1-imidazolyl)propionic acid, bromination to give 2-bromo-3-(1-imidazolyl)propionic acid, reaction with Na 2,6-dichlorothiophenolate to give 2-(2,6-dichlorophenylthio)-3-(1-imidazolyl)propionic acid, reduction with LiAlH4 to give the corresponding alcohol, and reaction with PBr3 ], 8 g of NaOH and 400 ml of ethanol is heated at 100° for 10 hours. The mixture is evaporated, worked up as usual and Ia of m.p. 175°-177° is obtained.

Provenance & Evidence