反应详情

Dicyclohexylcarbodiimide (11.05 g) was added in portions to a cooled, stirred mixture of 3-chloro-α-hydroxybenzeneacetic acid (10 g), 1,1-dimethylethanamine (3.92 g, 5.63 ml) and 1-hydroxybenzotriazole (7.24 g) in dry dimethylformamide (100 ml). The mixture was stirred at ambient temperature for 20 h., filtered and the filtrate evaporated. The residual oil was taken up in ethyl acetate, filtered, and the filtrate washed sequentially with sodium carbonate solution, hydrochloric acid (2N) and water. The organic layer was dried (MgSO4), filtered, and evaporated to an oil which was chromatographed on silica. Elution with chloroform gave N-[1,1-dimethylethyl]-3-chloro-α-hydroxybenzeneacetamide, 1.71 g, as an oil which crystallized in standing, m.p. 93°-99° C.

1. stirringThe mixture was stirred at ambient temperature for 20 h.
2. filtrationfiltered
3. customthe filtrate evaporated
4. filtrationfiltered
5. washthe filtrate washed sequentially with sodium carbonate solution, hydrochloric acid (2N) and water
6. dry with materialThe organic layer was dried (MgSO4)
7. filtrationfiltered
8. customevaporated to an oil which
9. customwas chromatographed on silica
10. washElution with chloroform