Reacción #47797

Ecuación de reacción

methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

dimethylformamide dimethyl acetal

→

title compound

Methyl 5-(4-chlorophenyl)-3-((dimethylamino)methyleneamino)thiophene-2-carboxylate

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroyielded 2.52 g (100%)
2. 2
   Otroafter removal of the volatiles under vacuum
3. 3
   Otro2.45 min retention time

Procedimiento

The title compound was prepared following the procedure described in WO2003/033476. Condensation of 2.00 g of methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate with dimethylformamide dimethyl acetal for 3 hr in refluxing EtOH yielded 2.52 g (100%) after removal of the volatiles under vacuum. 1H NMR (CDCl3) δ 3.06 (s, 3H), 3.08 (s, 3H), 3.81 (s, 3H), 6.98 (s, 1H), 7.35 (d, J=8.79 Hz, 2H), 7.53 (d, J=8.24 Hz, 2H), 7.69 (s, 1H); 13C NMR (CDCl3) δ 34.31, 40.26, 51.44, 112.43, 122.28, 126.95, 129.09, 132.18, 134.45, 145.79, 156.09, 159.16, 163.22. HPLC (Method #1): 2.45 min retention time. MS (ES): m/z 323 [M+H]+.

Fuente