Tert-Butylamine → N-[1,1-dimethylethyl]-3-chloro-alpha-hydroxybenzeneacetamide

Participants

Reaction Steps

Dicyclohexylcarbodiimide (11.0Sg) was added in portions to a cooled, stirred mixture of 3-chloro-α-hydroxybenzeneacetic acid (10g), 1,1-dimethylethanamine (3.92g, 5.63ml) and 1-hydroxybenzotriazole (7.24g) in dry dimethylformamide (100ml). The mixture was stirred at ambient temperature for 20h., 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, 1.71g, as an oil which crystallized on standing, m.p. 93-99° C.

Provenance & Evidence