Hydrochloric Acid → HCID 23370053, compound

Participants

Reaction Steps

A mixture of isopropyl 4-[3-(4-amidinobenzoyl)ureido]-3-methylphenoxyacetate, acetate salt (500 mg), water (50 ml), 50% aqueous acetic acid (1.5 ml) and 2N HCl (1.5 ml) was stirred and heated to 90°-100° C. until all the solids had dissolved. The hot solution was then quickly filtered and the filtrate was heated to 80°-85° C. and stored at that temperature for 3 days. The mixture was cooled and the solid was collected, washed thoroughly with water, methanol and with ether. The solid was suspended in refluxing methanol/dichloromethane, 4:1 (50 ml). The insoluble material was collected, washed with hot methanol and with ether and dried to give the title compound (250 mg), as a pale yellow solid: NMR Spectrum (DMSO-d6 +CF3CO2H) 2.30 (3H, s), 4.66 (2H, s), 6.81 (1H, dd), 6.89 (1H, d), 7.78 (1H, d), 7.97 (2H, d), 8.24 (2H, d), 9.17 (2H, br s), 9.48 (2H, br s), 10.51 (1H, s), 11.25 (1H, s); m/Z 371 (M+H)+ ; Elemental Analysis: calculated for C18H18N4O5. 1.25 H2O: C, 55.0%; H, 5.26%; N, 14.3%; found: C, 54.9%; H, 5.3%; N, 14.2%.

Provenance & Evidence