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

HRID 1283936

Reaction equation

HRID 1283936 reaction equation
CS[C:3]1[O:4][CH2:5][CH2:6][CH2:7][N:8]=1.[N+:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])([O-:11])=[O:10]>[Cl-].[Zn+2].[Cl-]>[N+:9]([C:12](=[C:3]1[NH:8][CH2:7][CH2:6][CH2:5][O:4]1)[C:13]([O:15][CH3:16])=[O:14])([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 17206Methyl 2-nitroacetateHCID 218167185,6-dihydro-2-(methylthio)-4H-1,3-oxazine

Product 1

HCID 71444191Methyl nitro(1,3-oxazinan-2-ylidene)acetate

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

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°.

Workup

  1. temperaturemaintained at that temperature for an additional hour
  2. temperatureThe mixture then was cooled
  3. customtriturated with ether
  4. customcrystallization
  5. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-c9185385c0a245acabbfac2212c48638
Source dataset
uspto-grants-1976_08
Patent number
US03976772

Linked notes

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