Acetone → HCID 131719654, compound

Participants

Reaction Steps

In a similar manner to Example 1, isopropyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]-3-methylphenoxyacetate (12.23 g) was reacted with iodomethane (100 ml) and acetone (750 ml) at ambient temperature and the resultant product was treated with ammonium acetate (15.4 g), methanol (350 ml) and dichloromethane (300 ml) at ambient temperature for 3 days and then at reflux for 5 hours. The mixture was filtered whilst hot, diluted with ether to turbidity and stored overnight at 10° C. to give a solid which was collected, washed with methanol/dichloromethane/ether, 1:1:2 (100 ml) and with ether and dried to give the title compound (7.88 g) as a pale yellow solid: NMR Spectrum (DMSO-d6) 1.23 (6H, d), 2.28 (3H, s), 4.71 (2H, s), 5.01 (1H, m), 6.77 (1H, dd), 6.86 (1H, d), 7.78 (1H, d), 7.91 (2H, d), 8.15 (2H, d), 10.55 (1H, br s); Elemental Analysis: calculated for C21H24N4O5. 1.0 CH3CO2H. 0.21H2O: C, 58.0%; H, 6.01%; N, 11.8%; found: C, 57.4%; H, 6.1%; N, 11.5%.

Provenance & Evidence