Dimethylthiocarbamoyl chloride → HCID 25228497, compound

Participants

Reaction Steps

Referring now to FIG. 22, under nitrogen, dimethylthio-carbamoyl chloride (1.35 g, 10.95 mmol) and DMAP (1.33 g, 10.95 mmol) were added to a suspension of 4 (300.0 mg, 0.628 mmol) in CH2Cl2 (6 mL). The dark brown solution was stirred for 24 h before it was diluted with chloroform and purified by column chromatography (4:6 to 1:1 EtOAc/hexane) to provide 16 (299 mg, 0.929 mmol, 64%) as an off-white solid: 1H NMR (CDCl3) δ 8.05, (1H, d, J=8.4 Hz), 7.78 (1H, d, J=8.8 Hz), 7.67 (1H, d, J=2.4 Hz), 7.29 (1H, dd, J=8.0, 2.8 Hz), 7.27, (1H, dd, J=8.4, 3.6 Hz), 3.48 (3H, s), 3.40 (3H, s), 2.73 (3H, s); 13C NMR (CDCl3) δ 187.6, 159.9, 154.7, 148.6, 136.2, 128.3, 124.8, 122.7, 122.1, 120.9, 43.5, 39.1, 25.6; FTIR (neat) 3379, 2940, 1624, 1603, 1531, 1504, 1393, 1283, 1206, 1169, 1130, 843, 748 cm−1; MS (ESI) m/z calculated for (C13H14N2OS+H)+ 247, found 247; HRMS (ESI) m/z calculated for (C13H14N2OS+H)+ 247.0905, found 201.0900.

Provenance & Evidence