Isopropyl Isothiocyanate → HCID 86725121, compound

Participants

Reaction Steps

To a suspension of 3-nitro-1H-indole-5-carbohydrazide (1.2 g, 5.454 mmol) in DMF (5 mL) was added isopropyl isothiocyanate (661 mg, 6.545 mmol) in one lot and the reaction was heated to reflux for 4 h. The mixture was quenched with water (20 mL) to get a pale yellow precipitate. The precipitate was filtered, washed with water (2×10 mL) and dried. The crude product was treated with 20% EtOAc in petroleum ether (2×20 mL) to afford N-isopropyl-2-(3-nitro-1H-indole-5-carbonyl)hydrazinecarbothioamide (1.5 g, 88%) as pale yellow solid. MS (ESI, pos. ion) m/z: 322.1 (M+1); 1H-NMR (300 MHz, DMSO-d6): δ 12.90 (brs, 1H), 10.43 (brs, 1H), 9.19 (s, 1H), 8.75 (s, 1H), 8.71 (s, 1H), 7.87-7.93 (m, 1H), 7.76 (d, 1H, J=8.4 Hz), 7.62 (d, 1H, J=8.4 Hz), 4.40-4.53 (m, 1H), 1.11 (d, 6H, J=6.6 Hz).

Provenance & Evidence