N,N-dimethyl-2-sulfanylbenzamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5-dichloro-4-nitro-phenylamine (17) (3.0 g, 14.5 mmol) and 2-mercapto-N,N-dimethyl-benzamide (3.0 g, 16.6 mmol) in DMF (50 mL) was heated to reflux with potassium carbonate (10 g) for 24 h. The mixture was poured into ice water and the precipitate was collected by a filtration. A dark colored solid was recrystalized from petroleum ether/methylene chloride yielded 3.8 g of (18) as a pale yellow powder (75%): IR (cm−1, KBr) 3461, 3376, 3153, 3154, 1627, 1575, 1492, 1135; 1H NMR (200 MHz CDCl3) δ 8.23 (s, 1H), 7.3–7.6 (m, 4H), 6.16 (s, 1H), 4.8 (br s, 2H), 3.37 (s, 3H), 2.86 (s, 3H). Anal. (C15H14ClN3O3S) C, H, N. the precipitate was collected by a filtration A dark colored solid was recrystalized from petroleum ether/methylene chloride