Isobutylamine → 5-amino-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Aminomalononitrile p-toluenesulfonate (25.33 g, 0.100 mol), triethylamine (10.12 g, 0.100 mol), and trimethyl orthobutyrate (14.82 g, 0.11 mol) were combined in toluene (250 mL) and the solution was heated at 60° C. for 1.75 hours. Additional trimethyl orthobutyrate (1.0 mL) was added, and the reaction was allowed to cool over a period of 1.5 hours to 22° C. and further cooled to about 3° C. Triethylamine (10.12 g, 0.100 mol) and isobutylamine (7.32 g, 0.100 mol) were sequentially added, and the reaction was warmed to room temperature slowly and stirred overnight. The reaction mixture was shaken with 10% w/w aqueous sodium carbonate (250 mL), and the mixture was allowed to stand for two hours. A precipitate was present and was isolated by filtration, washed sequentially with toluene and water, air-dried, and further dried under vacuum at 75° C. for 22 hours to provide 14.5 g (70%) of 5-amino-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile as a beige solid, mp 135.0-136.0° C.

Provenance & Evidence