Benzene → HCID 19787190, compound

Participants

Reaction Steps

To a mixture of 4-acetoxy-3,5-dimethylbenzoic acid (270 mg), diphenylphosphoryl azide (DPPA, 430 mg) and benzene (6 ml) was added dropwise triethylamine (0.18 ml) and the mixture was stirred at room temperature for 30 minutes and then at reflux for 40 minutes to obtain a solution of 4-acetoxy-3,5-dimethylphenylisocyanate. To the solution was added 5-amino-2-ethyl-4-(2-methoxyphenyl)-thieno[2,3-b]pyridine (284 mg) and the mixture was heated under reflux for 5 hours. The mixture was washed with water and dried over MgSO4 and the solvent was distilled off. To the residue was added ethanol to obtain N-(4-acetoxy-3,5-dimethylphenyl)-N'-[2-ethyl-4-(2-methoxyphenyl)thieno[2,3-b]pyridin-5-yl]urea (350 mg, 71.6%) as crystals. The crystals were recrystallized from ethanol to obtain colorless needles, mp: 217°-218° C.

Provenance & Evidence