4-Toluenesulfonyl chloride → 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole

Participants

Reaction Steps

To a solution of 2-(3-iodo-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole (7.0 g, 18.7 mmol) in DMF (70 mL) was added NaH 60% in mineral oil (1.5 g, 37.4 mmol) followed by TsCl (5.3 g, 28.1 mmol). The reaction was stirred at RT for 8 h, and the mixture was then poured into ice/H2O. The resulting precipitate was filtered, washed with water and dried to give 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole (7.7 g, 78%). MS (ESI, pos. ion) m/z: 528 (M+1); 1H-NMR (DMSO-d6, 300 MHz): 2.3 (s, 3H), 2.8 (s, 3H), 7.4 (d, 2H) 7.8 (d, 1H) 7.95 (m, 3H), 8.1 (d, 1H), 8.25 (s, 1H).

Provenance & Evidence