Cyanamide → 2-Amino-4-undecyloxazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-hydroxy-2-tridecanone (1.0 g, 4.7 mmol) and cyanamide (0.2 g, 5 mmol) in THF (3.0 mL) was added aqueous sodium acetate (2.0 mL, 1.0 N), tetra n-butylammoniumhydroxide (0.6 mL, 0.4 N 0.2 mmol), and sodium hydroxide (0.2 mL, 1.0 N, 0.2 mmol) sequentially. The resulting two-phase mixture was stirred (48 hours, 25° C.). The resulting mixture was taken up in ethyl acetate (200 mL), washed with brine (2×65 mL), dried (MgSO4), and concentrated in vacuo. The residue was chromatographed on silica (pure chloroform to 95:5 chloroform:methanol) and concentrated in vacuo to yield 0.70 g (63%) of the title compound as an off-white powder, m.p. 55°-58° C.

Provenance & Evidence