Oxalyl chloride → 9-bromo-N-(2,4-dichlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Participants

Reaction Steps

To a solution of 9-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid (911 mg) in dichloromethane (20 mL) and DMF (1 drop) was added oxalyl chloride (0.42 mL) and the reaction stirred at room temperature for 3 h. The solvent was then reduced in vacuo and the residue redissolved in acetonitrile. Sodium hydrogen carbonate (259 mg) and 2,4-dichloro-N-methylaniline (546 mg) were added and the reaction stirred at room temperature for 16 h. Water (20 mL) was added and the product extracted into ethyl acetate (2×20 mL). The organics were dried (MgSO4), reduced in vacuo and purified on silica to give 356. NMR: (CDCl3): 2.95-2.98 (2 H, m), 3.29 (3 H, s, Me), 4.13-4.16 (2 H, m), 6.72 (1 H, s, Ar), 6.78 (1 H, d, J 8.6, Ar), 7.16 (1 H, dd, J 8.6 and 2.3, Ar), 7.22 (1 H, d, J 8.5, Ar), 7.29 (1 H, dd, J 8.4 and 2.2, Ar) and 7.48-7.52 (1 H, m, Ar)

Provenance & Evidence