Methyl p-toluenesulfonate → 2-(5-acetyl-2-ethylamino-phenylimino)-3-benzyl-5-[(N-methyl-phenylamino)-methylene]-thiazolidin-4-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzyl-5-[(N-methyl-phenylamino)-methylene]-2-thioxo-thiazolidin-4-one (0.40 g, 1.2 mmol) and methyl p-toluenesulfonate (0.26 g, 1.4 mmol) in DMF (2 mL, anhyd) was heated at 125° C. After 2 h, the reaction mixture was cooled and an aliquot (0.4 mL) of the intermediate was transferred to an oven-dried vial. The intermediate was diluted with MeCN (2 mL, anhyd) and charged with 3′-amino-4′-ethylamino-acetophenone (53 mg, 0.30 mmol). The reaction mixture was warmed to 50° C., charged with TEA (100 μL), sealed and heated at 65° C. After 16 h, the reaction mixture was cooled, concentrated and chromatographed (silica gel, 0:100 to 50:50 EtOAc-Hex) to give the title product (14 mg) as a yellow solid. 1H-NMR (CDCl3): δ 7.92 (1H, s), 7.65 (1H, dd), 7.50 (1H, d), 7.27-7.42 (7H, m), 7.14-7.23 (3H, m), 6.48 (1H, d), 5.12 (2H, s), 4.27 (1H, br s), 3.51 (3H, s), 3.02 (2H, q), 2.45 (3H, s), 1.01 (3H, t); MS (ESI): 485 (MH+).

Provenance & Evidence