Acetonitrile → 3-{3-Benzyl-5-[3-methyl-4-methoxy-3H-benzothiazol-2-ylidene]-4-oxothiazolidin-2-ylideneamino}4-ethylaminobenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a suspension of the 4-methoxy2-methylthiobenzothiazole (0.60 g, 2.8 mmol) in anhydrous anisole (8 mL) was added methyl p-toluenesulfonate (1.4 mL, 9.0 mmol) and the suspension was heated at 130° C. for 3.5 h. After cooling to 20° C., MeCN (5 mL), 3-(3-benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylaminobenzonitrile (119 mg, 0.34 mmol) and TEA (2.0 mL, 14 mmol) were added. The suspension was stirred for 5 h at 80° C. After cooling to ambient temperature, yellow solids were collected by filtration, washed with MeCN and dried under high vacuum to afford the title compound (123 mg, 69%). 1H-NMR (CDCl3): δ 7.45–7.11 (9H, m), 6.88–6.85 (1H, m), 6.48 (1H, d), 5.17 (2H, s), 4.08 (3H, s), 3.92 (3H, s), 3.02–2.97 (2H, m), 1.02 (3H, t); MS (ESI): 528 (MH+).

Provenance & Evidence