Triethylamine → 2-(4-Chlorobenzoylamino)-4,5-dimethoxybenzamide

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>C1COCC1>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:1][C:2]2[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])=[O:28])=[CH:25][CH:24]=1

Participants

Procedure

To a solution of 2-amino-4,5-dimethoxybenzamide (2.0 g, 10.47 mmol) in THF (15 mL) and triethyl amine (3 mL, 20.91 mol) was added solution of 4-chlorobenzoyl chloride (2.2 g, 12.57 mol) in THF (5.0 mL) at rt for 10 min. The reaction mixture was stirred at rt 16 h. The solution was poured into ice cold water and stirred for 10 min. The separated solid was filtered, washed with ice cold water and dried to the product as a pale yellow color solid (2.9 g, 85%), mp 120-122° C. 1H NMR (400 MHz, DMSO-d6): δ 13.38 (1H, s), 8.48 (1H, br s), 8.33 (1H, br s), 7.94 (2H, d, J=8.0 Hz), 7.66 (1H, s), 7.65 (2H, d, J=8.0 Hz), 7.46 (1H, s), 3.84 (3H, s), 3.81 (3H, s); LC-MS (negative ion mode): m/z 333, 335 (M−H)−.