Acetone → HCID 23369998, compound

Participants

Reaction Steps

In a similar manner to Example 1, t-butyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate (4.4 g) was reacted with iodomethane (25 ml) and acetone (450 ml) and the resultant product was treated with ammonium acetate (10 g), methanol (400 ml) and dichloromethane (100 ml) at ambient temperature. This yielded a crude yellow solid (1.2 g), which was triturated with methanol, collected, washed with methanol and then stirred with 50% aqueous acetic acid solution (15 ml). Any solid material was filtered and discarded and the filtrate was evaporated and triturated under a mixture of ether and methanol to give the title compound (300 mg) as an off-white solid: NMR Spectrum (DMSO-d6) 1.44 (9H, s), 1.77 (1.8H, s), 4.62 (2H, s), 6.90 (2H, d), 7.49 (2H, d), 7.92 (2H, d), 8.15 (2H, d), 9.50-10.4 (3H, br), 10.60 (1H s); Mass Spectrum m/Z 413 (M+H)+ ; Elemental Analysis: calculated for C21H24N4O5. 0.6 CH3CO2H. 1.5 H2O: C, 56.0%; H, 6.2%; N, 11.7%; found: C, 56.3%; H, 6.2%; N, 11.1%.

Provenance & Evidence