Dichloromethane → N,2-dimethoxy-N-methylacetamide

HRID 2279500Notes

Reaction equation

HRID 2279500 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].C(Cl)Cl.Cl.[CH3:11][NH:12][O:13][CH3:14]>O>[CH3:14][O:13][N:12]([CH3:11])[C:4](=[O:5])[CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 96623Methoxyacetyl chloride

Product 1

HCID 14872187N,2-dimethoxy-N-methylacetamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-methoxyacetyl chloride (10 g, 92.1 mmol) and DCM (100 mL) cooled to 0° C. was added N,O-dimethylhydroxylamine hydrochloride (9.89 g, 101 mmol) and TEA (38.5 mL, 276 mmol) and the reaction warmed to RT and stirred for 18 h. The reaction mixture was poured into H2O and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated to give the crude product, which was purified by SiO2 chromatography eluting with DCM/MeOH (500:50) to afford 12 g (97.8%) of N,2-dimethoxy-N-methylacetamide.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by SiO2 chromatography
  7. washeluting with DCM/MeOH (500:50)

Sources & evidence

ORD record
ord-fa7dd4583f484d64a6a105b1d33e8553
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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