Cyclohexanone → (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(5-bromothiophen-2-yl)-methanone

Participants

Reaction Steps

The procedure of Example 1 was followed except that 2-acetyl-5-bromothiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(5-bromothiophene-2-carbonyl)acetonitrile (Steps A and B). Cyclohexanone (Aldrich), 2-(5-bromothiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 66%; IR (KBr) cm−1: 3379, 3247, 2918, 1577, 1548, 1432, 1416, 1273, 761; 1H NMR (CDCl3):δ1.63 (m, 2H), 1.79 (m, 2H), 2.24 (t, 2H, J=5.8 Hz), 2.55 (t, 2H, J=5.8 Hz), 6.11 (bs, 2H), 7.02 (d, 1H, J=4 Hz), 7.13 (d, 1H, J=4 Hz); orange solid, mp: 160-163° C. (petroleum ether).

Provenance & Evidence