Acetone → HCID 131719659, compound

Participants

Reaction Steps

In a similar manner to Example 1, isopropyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate (10.88 g) was reacted with iodomethane (60 ml) and acetone (600 ml) at ambient temperature and the resultant product was treated with ammonium acetate (12 g), methanol (220 ml) and dichloromethane (220 ml). This yielded, after filtering the reaction mixture whilst hot and evaporating the filtrate to near dryness, a pale yellow solid, which was slurried in dichloromethane and stirred at ambient temperature overnight, filtered and the solid dissolved in hot methanol. After cooling, the precipitated solid was collected and washed with dichloromethane to give the title compound (2.4 g) as a pale yellow solid: m.p. >300° C. (decomposes); NMR Spectrum (DMSO-d6) 1.29 (6H, d), 4.77 (2H, s), 5.06 (1H, m), 6.97 (2H, d), 7.54 (2H, d), 7.97 (2H, d), 8.20 (2H, d), 10.75 (1H, br s); Mass Spectrum m/Z 399 (M+H)+ ; Elemental Analysis: calculated for C20H22N4O5. 1.0 CH3CO2H. 0.5 H2O: C, 56.5%; H, 5.8%; N, 12.0%; found: C, 56.7%; H, 5.9%; N, 11.9%.

Provenance & Evidence