Thiophosgene → HCID 86675384, compound

Participants

Reaction Steps

To a solution of compound (12) (0.79 g, 1.81 mmol) in 0.5 M HCl (10 ml) was carefully added thiophosgene (CSCl2) (4.17 ml, 6.26 g, 54.4 mmol) in CHCl3 (10 ml). The reaction mixture was stirred at an ambient temperature for 5 hours to separate the layers. After removing the aqueous layer, the organic CHCl3 layer was washed with water (2×50 ml). The combined aqueous layer was washed with CHCl3 (3×50 ml) to remove the unreacted thiophosgene. Finally, the aqueous layer was lyophilized to obtain a white solid of compound (14) (0.85 g, 98% yield). 1H NMR (500 MHz, D2O): δ 7.67-7.65 (dd, 2H), 7.50-7.48 (dd, 2H), 3.923 (s, 4H), 3.48-2.52 (m, 20H), 1.98 (brs, 2H), 1.88 (brs, 2H); 13C NMR (125 MHz, D2O): δ 187.9, 174.4, 173.2, 145.7, 137.5, 136.8, 135.1, 129.1, 128.6, 125.5, 122.6, 121.6, 60.4, 59.7, 57.8, 57.2, 56.9, 56.1, 54.5, 48.5, 35.5, 29.7, 23.3, 20.7; HRMS (FAB) calculated for C23H36N5O4S: 478.2488 [(M+H)+], measured value: 478.2484 [(M+H)+].

Provenance & Evidence