Ammonia → HCID 178442466, compound

Participants

Reaction Steps

Toluenesulfonylmethyl isocyanide (154 g, 0.9 mol) was added to a saturated solution of ammonia in methanol (7 L). After stirring at rt for 1 h, 3,3-dimethylpentanal (0.6 mol) was added over 20 min. After stirring at reflux for 3 h, the reaction mixture was poured into cold 1 N hydrochloric acid and washed with hexane. The aqueous layer was basified with 10 N aqueous sodium hydroxide and extracted with ether. The combined extracts were washed with brine, dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica gel eluting with 5-10% methanol/methylene chloride afforded 4-(2,2-dimethylbutyl)-1H-imidazole.

Provenance & Evidence