Phosphorus oxychloride → HCID 43805572, compound

Participants

Reaction Conditions

Reaction Steps

To an ice cooled mixture of 4-bromo-2-chlorobenzoic acid (2 g, 8.49 mmol) and hydrazinecarbothioamide (1.161 g, 12.74 mmol) was added phosphorous oxychloride (2.375 mL, 25.5 mmol) slowly, and the reaction was heated at 78° C. for 3 hours. After cooling to 0° C., ice water was added and the mixture was vigorously stirred for 1 hour. The resulting precipitate was filtered, washed with water then re-suspended in saturated NaHCO3(aq) and water (1:1) and stirred for 1 hour. The solid was filtered, washed with water, and dried in vacuo to afford the title compound which was used without further purification (2 g, 81% yield). MS m/z 291.9 [M+H]+, 1H NMR (400 MHz, DMSO-d6) δ ppm 7.80-8.09 (m, 2H), 7.68 (dd, J=2.02, 8.59 Hz, 1H), 7.55 (br. s, 2H).

Provenance & Evidence