Isopropanol → Methyl nitro(1,3-thiazinan-2-ylidene)acetate

Participants

Reaction Steps

To a mixture of 221 g of 5,6-dihydro-2-(methylthio)-4H-1,3-thiazine (A. F. McKay et al., J. Am. Chem. Soc., 80, 3339 (1950) and 1 g of zinc chloride at about 100°, 202 g of methyl nitroacetate (S. Zen et al., Kogyo Kagaku Zasshi, 74, 70 (1971)) was added dropwise over a 30-minute period. The resulting mixture was heated for 4 hours at 95°-105°. 200 ml of isopropyl alcohol then was added to the hot mixture, then 400 ml of ether was added. The resulting mixture was filtered to give methyl nitro(tetrahydro-2H-1,3-thiazin-2-ylidene)-acetate (1A), as a pale yellow solid, m.p.: 107°-108° C.

Provenance & Evidence