Thioglycolic Acid → 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamide

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Reaction Steps

A solution of N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 5 (500 mg, 1.704 mmol) in mercaptoacetic acid (3 mL, 43.2 mmol) was stirred at 100° C. for 2 h. Quenched with water and extracted with EtOAc. Organic layer was washed with NaHCO3 solution, brine, dried and evaporated. Purification by chromatography (0-4% methanol in CH2Cl2) gave pure 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamide 16 (500 mg, 80%). 1H-NMR (400 MHz, CDCl3) 1.78 (s, 6H), 2.31 (s, 3H), 3.45 (d, J=9.4 Hz, 2H), 7.21 (d, J=8.2 Hz, 1H), 7.52 (t, J=8.2 Hz, 1H), 7.70-7.79 (m, 3H), 7.92-8.08 (m, 3H), 8.67 (br s, 1H).

Provenance & Evidence