Furfurylamine → 4-chloro-N-(furan-2-ylmethyl)benzamide

Participants

Reaction Steps

A solution of 4-chlorobenzoyl chloride (3.2 g, 18.5 mol) in 50 ml dry CH2Cl2 was added over 30 min to a stirred solution of 2-furfurylamine (2 g, 20.6 mol) and iPr2NEt (7 ml, 41 mol) in CH2Cl2 (200 ml) at 0° C. The reaction was allowed to warm to room temperature over 3 h. The mixture was diluted with 200 ml of CH2Cl2, washed twice with HCl aq. (1N) and dried over MgSO4. Evaporation of the solvent afforded 4 g (83%) of the title benzamide as a white solid: 1H NMR: (DMSO-d6) δ 9.05 (t, J=5.7 Hz, 1H), 7.89 (d, J=8.7 Hz, 2H), 7.57 (m, 1H), 7.53 (d, J=8.7 Hz, 2H), 6.40 (dd, J=3.7, 1.1 Hz, 1H), 6.28 (d, J=3.7 Hz, 1H), 4.46 (d, J=5.6 Hz, 2H). M/Z APCI: 236.6 (M+1), 234.8 (M−1).

Provenance & Evidence