反应详情

4-(Methylthio)phenyl isocyanate (2.8 g, 17 mmol) was added to a stirring slurry of 3.8 g (3.0 mmol) of the product of Example 6 in methylene chloride (25 mL) at 21° C. causing rapid formation of a pale precipitate. TLC showed complete conversion after 19 hr and the precipitate, which was the corresponding bisaryl urea, was removed by gravity filtration. The filtrate was diluted with saturated aqueous sodium bicarbonate and the layers separated. The organic layer was dried over sodium sulfate, filtered, and evaporated to obtain a red oil which solidified on standing. This was purified by column chromatography eluting with 100:0 to 90:10 methylene chloride/ethyl acetate solvent. The product was recrystallized by dissolving in ethyl acetate and then adding hexane to obtain 0.44 g (29 percent of theory; 9 percent from the ethanone) of the title compound as fine white needles melting at 225°-226° C.;

1. customafter 19 hr
2. customwas removed by gravity filtration
3. additionThe filtrate was diluted with saturated aqueous sodium bicarbonate
4. customthe layers separated
5. dry with materialThe organic layer was dried over sodium sulfate
6. filtrationfiltered
7. customevaporated
8. customto obtain a red oil which
9. customThis was purified by column chromatography
10. washeluting with 100:0 to 90:10 methylene chloride/ethyl acetate solvent
11. customThe product was recrystallized
12. dissolutionby dissolving in ethyl acetate
13. customadding hexane to obtain 0.44 g (29 percent of theory