Pyridine → N-METHOXY-2,N-DIMETHYLACRYLAMIDE

HRID 534125Notes

Reaction equation

HRID 534125 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].N1C=CC=CC=1.[C:12](Cl)(=[O:16])[C:13]([CH3:15])=[CH2:14]>C1COCC1>[CH3:2][O:3][N:4]([CH3:5])[C:12](=[O:16])[C:13]([CH3:15])=[CH2:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13528Methacryloyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 11332477N-METHOXY-2,N-DIMETHYLACRYLAMIDEYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

O,N-dimethylhydroxylamine hydrochloride (74.6 g, 765 mmol) was dissolved in THF (1 L) and pyridine (123 ml, 1531 mmol) was added and stirred for 30 minutes. Methacryloyl chloride (37.4 ml, 383 mmol) was added slowly and stirred overnight. The solids were filtered and concentrated. The residue was partitioned between water and CH2Cl2, washed with water, dried over sodium sulfate, filtered and concentrated to afford N-methoxy-N-methylmethacrylamide (56.5 g, 335 mmol, 87.5% yield).

Workup

  1. stirringstirred overnight
  2. filtrationThe solids were filtered
  3. concentrationconcentrated
  4. customThe residue was partitioned between water and CH2Cl2
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-851afad4a5ce41c69677fd3eceaaa9b2
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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