Diethylamine → N,N-diethyl-4-(3-methoxybenzoyl)benzamide

Participants

Reaction Steps

A mixture of 0.23 grams of acid (3.1b), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.2 equivalents with respect to the acid) and 1-hydroxy benzotriazol hydrate (1.2 equivalents) in anhydrous CH2Cl2 (2 ml) is stirred at room temperature for 30 minutes. A solution of diethylamine (1.5 equivalents) in anhydrous CH2Cl2 (8 ml) is then dropwise added. The obtained mixture is stirred at room temperature for 14 hours and washed in a first step with saturated aqueous sodium bicarbonate and in a second step with water. The organic phase is dehydrated with sodium sulphate, filtered and evaporated under vacuum. The residue that is recovered is purified by flash chromatography (ligroin/ethyl acetate 1/1 v/v). N,N-diethyl-4-(3′-methoxybenzoyl)benzamide (3.1c) is obtained. Yield: 98%. IR (nujol) (λ=cm−1) 1690 (C═O); 1H-NMR (CDCl3) δ 1.00-1.38 (m, 6H); 3.20-3.38 (m, 2H); 3.50-3.70 (m, 2H); 3.86 (s, 3H); 7.10-7.40 (m, 4H); 7.48 (d, 2H, J=8.4 Hz); 7.84 (d, 2H, J=8.4 Hz). Anal. calc. for C19H21NO3: C, 73.29; H, 6.80; N, 4.50. Found: C, 73.11; H, 6.78; N, 4.49.

Provenance & Evidence