Acetyl chloride → (Methylnitramino)methylacetate

HRID 2081919

Reaction equation

HRID 2081919 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-aza-1-propanol 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 (MgSO4), 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. dry with materialdried (MgSO4)
  8. distillationdistilled

Sources & evidence

ORD record
ord-87c26324ad1d4bc7b0a8c702dd35ba7f
Source dataset
uspto-grants-1993_02
Patent number
US05186770

Linked notes

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