Diethyl chlorophosphate → ethyl (2Z)-2-[2-(diethoxyphosphorylamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetate

Participants

Reaction Steps

To a stirred solution of 4.6 g (0.02 mol) of ethyl 2-(aminothiazol-4-yl)-Z-2-methoxyiminoacetate in 40 ml pyridine at 10°-20° was added 9.0 ml (0.6 mol) diethyl chlorophosphate. The solution was stirred at room temperature for 2 hours. Pyridine was evaporated and the residue was codistilled with benzene and partitioned between water and methylene chloride. The methylene chloride layer was washed with excess 10% aqueous HCl, water, aqueous bicarbonate, saturated sodium chloride, and dried over sodium sulfate. Upon evaporation, 5.5 g brown oil was obtained which was purified on Biosil A using hexane/ethyl acetate (1:4) to afford 2.8 g of yellow crystals, m.p. 96.5-98.0; NMR (300MH2, DCCl3) δ 1.35 (3t, 9, CH3), 3.97 (S, 3, OCH3), 4.17 (q, 4, OCH2), 4.39 (q, 2, OCH2), 6.93 (s, 1, thiazole H).

Provenance & Evidence