N-dimethylaminomethylene-4-methyl-benzamide → 3-(4-p-Tolyl-[1,3,5]triazin-2-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

Part D. A mixture of N-dimethylaminomethylene-4-methyl-benzamide (221.9 mg, 1.15 mmol) and 3-carbamimidoyl-benzoic acid tert-butyl ester (196.0 mg, 0.89 mmol) in anhydrous acetic acid (8 mL) is heated to 115° C. at 150 W, 250 psi in a microwave reactor for 30 min. until complete consumption of the starting material is determined by TLC. A white solid is precipitated by addition of 1 N HCl, and collected by filtration, followed by washing with water and hexanes. The obtained solid is further purified by flash column chromatography, eluting with methanol/methylene chloride (1:20) to afford the title product (23.1 mg, 5.3% yield), m.p. 298-300° C. 1H NMR (300 MHz, DMSO-d6): δ 9.40 (1H, s), 8.63 (2H, d, J=8.3 Hz), 8.48 (2H, d, J=8.0 Hz), 8.13 (2H, d, J=8.0 Hz), 7.41 (2H, m), 2.41 (3H, s). MS (ES+): m/e 292.30.

Provenance & Evidence