Isobutylamine → HCID 6063397, compound

Participants

Reaction Steps

A solution of 3-chlorocinnamoyl chloride (4g) in dry toluene (75 ml) was added with stirring to a solution of isobutylamine (12 ml) in dry benzene (200 ml). The reaction mixture was allowed to stand for 24 hours. The solvent was evaporated under reduced pressure and the residue thoroughly triturated with water, washed with dilute hydrochloric acid and then with water. The resulting crude product was recrystallized from ethanol-water (1:10) to give trans 3-chloro-N-isobutylcinnamamide (3.9 g), m.p. 111.5°-112.5° C. Elemental analysis, nmr and ir data were all consistent with the assigned structure. TLC gave one spot run on silica gel with 5:1 and 3:1 hexane:ethanol.

Provenance & Evidence