O-Phenylenediamine → Methyl 2-{[(2-aminophenyl)amino]carbonyl}-1-benzothiophene-6-carboxylate

Participants

Reaction Steps

To a solution of benzo[b]thiophene-2,6-dicarboxylic acid 6-methyl ester (129 mg, 0.543 mmol) in DMF (4 mL) was added EDCI (125 mg, 0.652 mmol), HOBt (88 mg, 0.652 mmol). The reaction mixture was stirred for 20 min and phenylene diamine (147 mg, 1.36 mmol) was added. After 18 h, the solvent was removed and EtOAc and H2O were added. The resultant solid was filtered yielding the desired product. 1H NMR (CDCl3, 600 MHz) δ 8.53 (s, 1H), 8.01 (s, 1H), 7.99 (d, J=7.9 Hz, 1H), 7.86 (d, J=7.9 Hz, 1H), 7.23 (d, J=6.8 Hz, 1H), 7.05 (t, J=6.8 Hz, 1H), 6.81 (d, J=6.8 Hz, 1H), 6.80 (t, J=6.8 Hz, 1H), 3.90 (s, 3H). MS: cal'd 327 (MH+), exp 327 (MH+).

Provenance & Evidence