Ammonia → HCID 21504226, compound

Participants

Reaction Steps

A mixture of 4-fluorophenylacetonitrile (71 g.) and dry ethanol (27.6 g.) was cooled in an ice-bath and dry hydrogen chloride was passed in until a weight increase of 25.5 g. was obtained. The mixture was allowed to stand at room temperature for 3 days and then treated portionwise, with vigorous shaking and occasional cooling, with a saturated solution of ammonia in dry ethanol. Addition was continued until a smell of ammonia persisted. The mixture was allowed to stand at room temperature for 2 days and then filtered. The filtrate was treated with a saturated aqueous solution of 1.1 equivalents of sodium p-toluenesulphonate and diluted with water. The crystalline precipitate was removed and recrystallised from ethanol to give pure 4-fluorophenylacetamidine p-toluenesulphonate, m.p. 215°-218°. The following amidines were also prepared by Method E; crystallisation solvents are given in brackets:

Provenance & Evidence