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

Temperature

50 °C

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).

1. stirringthe reaction mixture was stirred at 50° C. for 15 min
2. filtrationthe solid was filtered
3. washwashed with more water and ether
4. customto give a white solid
5. customMeOH was removed under reduced pressure
6. washthe solid was washed with water and ether
7. customto give III-b as a white solid in 78% yield

ORD record

ord-852c2d0d26ee4266979d91a56b73008c

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09168245B2