Acetyl chloride → (5-methoxy-2-methyl-phenyl)thiourea

Participants

Reaction Conditions

Reaction Steps

To a solution of KSCN (780 mg, 8.02 mmol) in acetone (10 mL) was added dropwise at room temperature as solution of AcCl (900 μL, 8.02 mmol) in acetone (10 mL). The reaction mixture was stirred for 15 min at 50° C. Then, a solution of 5-methoxy-2-methylaniline (1.0 g, 7.29 mmol) in acetone (10 mL) was added and the reaction mixture was stirred at 50° C. for 15 min. Water was added and the solid was filtered, washed with more water and ether to give a white solid. A solution of the latter with K2CO3 (2.0 g, 14.58 mmol) in MeOH (20 mL) was stirred at room temperature for 3 h. MeOH was removed under reduced pressure and the solid was washed with water and ether to give III-b as a white solid in 78% yield. 1H NMR (300 MHz, DMSO-d6) δ 9.20 (s, 1H), 7.13 (d, J=8.4 Hz, 1H), 6.81 (d, J=2.4 Hz, 1H), 6.75 (dd, J=8.3, 2.6 Hz, 1H), 3.71 (s, 3H), 2.10 (s, 3H).

Provenance & Evidence