Diiodomethane → HCID 58500138, compound

Participants

Reaction Conditions

Reaction Steps

A solution of isoamylnitrite (96 mL, 715 mmol), diiodomethane (475 mL), and chloroform (240 mL) was heated to 80° C. over a period of one hour. A solution of tert-butyl 2-[2-(5-amino-4-cyano-2-propyl-1H-imidazol-1-yl)ethoxy]ethylcarbamate (64.3 g, 191 mmol) in chloroform (240 mL) was added dropwise over a period of 115 minutes. During the addition the reaction temperature was decrease to 74° C. The reaction was allowed to cool to 50° C., and the chloroform was removed under reduced pressure. The resulting liquid was diluted with a small volume of dichloromethane and was purified by chromatography on silica gel (eluting sequentially with hexanes and ethyl acetate) and dried under high vacuum at 60° C. for eight hours to provide 56.3 g (66%) of tert-butyl 2-[2-(4-cyano-5-iodo-2-propyl-1H-imidazol-1-yl)ethoxy]ethylcarbamate as a dark orange oil containing a small amount of diiodomethane.

Provenance & Evidence