Oxalyl chloride → HCID 23370021, compound

Participants

Reaction Steps

To a stirred suspension of 6-cyanonicotinamide (Synthesis (1983), 316) (1.2 g) in 1,2-dichloroethane (28 ml) was added oxalyl chloride (1.3 ml) and the mixture was heated at reflux with stirring for 2.5 hours. The reaction mixture was cooled and the solvents were removed in vacuo to yield 6-cyanonicotinoyl isocyanate as a yellow solid residue. Then in a similar manner to Example 1, starting material step (a), this residue, t-butyl 4-aminophenoxyacetate, acetate salt (1.59 g), triethylamine (3.8 ml) and acetonitrile (140 ml total) gave, after stirring at ambient temperature for 3 hours followed by evaporation of the solvents, a yellow solid, which was collected, washed with cold acetonitrile and with hexane and dried to give t-butyl 4-[3-(6-cyanopyrid-3-ylcarbonyl)ureido]phenoxyacetate (2.37 g): m.p. 220°-222° C. (decomposes); NMR Spectrum (DMSO-d6) 1.48 (9H, s), 4.67 (2H, s), 6.94 (2H, d), 7.52 (2H, d), 8.27 (1H, d), 8.58 (1H, dd), 9.25 (1H, d), 10.41 (1H, s), 11.40 (1H, s); Mass Spectrum m/Z 396 (M+).

Provenance & Evidence