反应详情

温度

50 °C

Methyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate (870 mg) was suspended in acetone (100 ml) and iodomethane (10 ml) was added. The stirred suspension was heated to 50° C. After 24 and 48 hours respectively, two further aliquots of iodomethane (10 ml+10 ml) were added whilst stirring at 50° C. was continued. Removal of the solvents in vacuo yielded methyl 4-[3-(4-(methylthio)carbonimidoylbenzoyl)ureido]phenoxyacetate as an orange-brown solid residue which was not purified further. The residue was suspended in methanol (40 ml) and heated to 45°-50° C. with stirring before a solution of ammonium acetate (1.54 g) in methanol (20 ml) was added. After stirring overnight at 45°-50° C., extra portions of methanol (10 ml) and ammonium acetate (0.77 g) were added and the reaction mixture was heated to 70° C. with stirring. After stirring for a further 24 hours at 70° C., the solvents were removed in vacuo to yield a pale yellow solid which was crystallised, with filtration, from boiling methanol to give the title compound (208 mg) as an off-white solid: NMR Spectrum (DMSO-d6) 1.78 (3H, s), 3.71 (3H, s), 4.77 (2H, s), 6.93 (2H, d), 7.50 (2H, d), 7.91 (2H, d), 8.14 (2H d) 9.00-11.00 (3H br); Mass Spectrum m/Z 371 (M+H)+ ; Elemental Analysis: calculated for C18H18N4O5. 1.0 CH3CO2H. 0.75 H2O: C, 54.1%; H, 5.34%; N, 12.6%; found: C, 54.3%; H, 5.0%; N, 12.3%.

1. customRemoval of the solvents in vacuo