Acetyl chloride → (Methylnitramino)methylacetate

HRID 1285556

Reaction equation

HRID 1285556 reaction equation
[N+:1]([N:4]([CH3:7])[CH2:5][OH:6])([O-:3])=[O:2].[C:8](Cl)(=[O:10])[CH3:9]>ClCCl>[C:8]([O:6][CH2:5][N:4]([N+:1]([O-:3])=[O:2])[CH3:7])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 119262Methanol, (methylnitramino)-

Product 1

HCID 147637(Methylnitramino)methylacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 10.6 g of 2-nitro-2-azapropanol and 25 ml of dichloromethane under a nitrogen atmosphere was added dropwise and with ice-cooling 12 g of acetyl chloride. The cooling bath was removed and the mixture was slowly heated to reflux. After 3 hours the solution was allowed to cool and was then triturated with 50 ml of ice water. The organic phase was separated, dried (MG SO4), and distilled. The product 2-nitro-2-azapropyl acetate had b.p. 56°-57° C. at 0.07 mm Hg.

Workup

  1. additionwas added dropwise and with ice-
  2. customThe cooling bath was removed
  3. temperaturethe mixture was slowly heated to reflux
  4. temperatureto cool
  5. customwas then triturated with 50 ml of ice water
  6. customThe organic phase was separated
  7. customdried (MG SO4)
  8. distillationdistilled

Sources & evidence

ORD record
ord-d39d401e85144d65ac55ddcdc5ccb1da
Source dataset
uspto-grants-1986_01
Patent number
US04567296

Linked notes

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