Hydrochloric Acid → HCID 18630996, compound

Participants

Reaction Steps

To a solution of 4-(4-methylpyridin-2-yl)benzaldehyde oxime (0.41 g) in N,N-dimethylformamide (2 ml) were added a solution of hydrogen chloride in 1,4-dioxane (4N, 1.06 ml) and potassium peroxymonosulfate (OXONE, 0.712 g). The reaction mixture was stirred for 1.5 hours, and to the mixture were added tetrahydrofuran (10 ml) and thiourea (0.176 g). Then to the resultant suspension was added a solution of triethylamine (0.673 ml) in tetrahydrofuran (2 ml) dropwise, and the mixture was stirred for 1 hour. The mixture was poured into water (100 ml) and extracted with ethyl acetate (100 ml). The separated aqueous layer was extracted with ethyl acetate (50 ml). The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (5 ml), and to the solution was added aqueous ammonia (28%, 3 ml) dropwise. The mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. To the residue was added dichloromethane and diisopropyl ether, and the precipitate was collected by filtration and dried to give N-(4-(4-methylpyridin-2-yl)-phenyl)thiourea (206 mg).

Provenance & Evidence