Phosgene → HCID 178431818, compound

Participants

Reaction Conditions

Reaction Steps

A 20% solution of phosgene in toluene (715 μl) was added to a stirred and cooled solution of N-(2-amino-4-methyl-3-thienylsulfonyl)-N′-isopropylthiourea (0.22 g) and triethylamine (313 μl) in dry THF (5 ml) the temperature being kept below 5° C. After stirring for 1.5 h the mixture was evaporated and triturated with 10 ml of water. The precipitate was collected by filtration and dried to give 0.14 g of crude product. The crystals were heated at 70° C. with 5 ml of ethyl acetate and the resulting mixture was cooled to 0° C. for 10 min and then filtered. The filter cake was rinsed with a minute amount of ethyl acetate and dried to give 0.087 g (yield 45%) of the title compound as tan crystals; m.p. 152-154° C.; 1H-NMR (DMSO-d6): δ(ppm): 7.10 (br d, 1 H, NH), 6.61 (s, 1 H, N(4)H), 6.52 (s, 1 H, C(6)H), 3.89 (m, 1 H, CH), 2.32 (s, 3 H, CH3), 1.18 (d, 6 H, CH3).

Provenance & Evidence