Benzoyl chloride → N-Propylbenzamide

Participants

Reaction Conditions

Reaction Steps

Dry DCM (30 mL) was added to benzoyl chloride (2.06 mL, 17.7 mmol) followed by the dropwise addition of propylamine (3.19 mL, 38.9 mmol) over 5 min at 0° C. The system was stirred at 0° C. under nitrogen for 1 h and monitored by TLC. After 1 h the system was washed with 1M HCl (20 mL), brine (10 mL) and dried with MgSO4. The solvent was removed to give N-Propylbenzamide as a white solid (2.6 g, 15.9 mmol, 90%); Rf 0.38 (40:60 EtOAc:petrol). mp 87.6-88.9° C. Lit. 83-84° C.7 1H NMR: (300 MHz, CDCl3) δ 0.90 (t, 3H, J=7.4 Hz, CH2—CH2—CH3), 1.56 (sex, 2H, J=7.2 Hz, N—CH2—CH2), 3.33 (m, 2H, N—CH2), 6.21 (bs, 1H, NH), 7.31-7.43 (m, 3H, Ar—H), 7.69 (m, 2H, Ar—H). 13C NMR: (75 MHz, CDCl3) δ 11.8, 23.3, 42.1, 127.2, 128.8, 131.6, 135.2, 167.9. LC/MS-ES+ m/z 164.2 [MH+], 327.1, 328.1.

Provenance & Evidence