Methyl 2-nitroacetate → Methyl nitro(1,3-oxazinan-2-ylidene)acetate

Participants

Reaction Steps

A mixture of 25 g of 5,6-dihydro-2-(methylthio)-4H-1,3-oxazine (Clapp, et al., J. Heterocyclic Chemistry, 5, 107 (1968)), 25 g of methyl nitroacetate and a catalytic amount of zinc chloride was heated to 90° over one hour and maintained at that temperature for an additional hour. The mixture then was cooled and triturated with ether to effect crystallization. The solid was recrystallized from ethanol to give methyl nitro(tetrahydro-2H-1,3-oxazin-2-ylidene)acetate (1A), as a yellow solid, m.p.: 132°-3°.

Provenance & Evidence