Diethyl Ether → 1-(3-Benzoyl-thioureido)-1H-pyrrole-2-carboxylic acid ethyl ester

Participants

Reaction Steps

1-Amino-1H-pyrrole-2-carboxylic acid ethyl ester (53.0 g, 0.344 mol) was dissolved in Tetrahydrofuran (2000 mL). Benzoyl isothiocyanate (56.1 g, 0.344 mol) was added and the reaction was allowed to stir overnight. The reaction mixture was reduced and 55.47 grams of 1-(3-Benzoyl-thioureido)-1H-pyrrole-2-carboxylic acid ethyl ester was isolated as a white solid via trituration with ether. (M+Na)=339.98. 1H NMR (400 MHz, DMSO, d6) δ 12.91 (s, 1H), 11.94 (s, 1H), 7.98 (d, 1H, J=7.32 Hz), 7.68 (t, 1H, J=7.52 Hz), 7.56 (t, 2H, J=7.64 Hz), 7.16 (m, 1H), 6.89 (m, 1H), 6.19 (m, 1H), 4.14 (q, 2H, J=7.12 Hz), 1.18 (d, 3H, J=14.17 Hz).

Provenance & Evidence