N-Methylacetamide → N-alpha-methoxyethyl-N-methyl-acetamide

HRID 1156201Notes

Reaction equation

HRID 1156201 reaction equation
C(N(CC)CC)C.[CH3:8][NH:9][C:10](=[O:12])[CH3:11].[CH3:13][O:14][CH:15](Cl)[CH3:16].[OH-].[Na+]>CCCCCC>[CH3:13][O:14][CH:15]([N:9]([CH3:8])[C:10](=[O:12])[CH3:11])[CH3:16]

Participants

6

Reactant 4

HCID 6582N-MethylacetamideHCID 8471Triethylamine2×HCID 14798Sodium Hydroxide2×HCID 1370671-Chloro-1-methoxyethane

Product 1

HCID 21464473N-alpha-methoxyethyl-N-methyl-acetamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

First 20 g of triethylamine and then a mixture of 91 g of triethylamine (1.1 moles in total) and 36.5 g (0.5 mole) of N-methylacetamide are added dropwise, at 0° C., to a solution of 94.5 g (1 mole) of α-chloroethyl methyl ether in 200 ml of hexane. After 2 hours, 44 g (1.1 moles) of technical-grade sodium hydroxide flakes are added and 20 ml of 50% strength sodium hydroxide solution are added dropwise, whilst cooling with ice, and the mixture is stirred for a further half an hour. The hexane solution is decanted, the flask is rinsed with hexane and the reaction solution is concentrated, the triethylamine employed being completely recovered in the distillate. The residue is subjected to flash distillation in vacuo. This yields 61 g (93% of theory) of N-α-methoxyethyl-N-methyl-acetamide. Boiling point (23 mm Hg): 84° C. 1H-NMR (CDCl3): 1.2-1.4 ppm (dd); 2.1 ppm (d); 2.8 ppm (d); 3.2 ppm (d); 4.95-5.15 ppm (q); 5.6-5.9 ppm (q).

Workup

  1. temperaturewhilst cooling with ice
  2. customThe hexane solution is decanted
  3. washthe flask is rinsed with hexane
  4. concentrationthe reaction solution is concentrated
  5. distillationthe triethylamine employed being completely recovered in the distillate
  6. distillationThe residue is subjected to flash distillation in vacuo
  7. custom84° C

Sources & evidence

ORD record
ord-0a7d1996f3924a708ee293d020f44955
Source dataset
uspto-grants-1982_06
Patent number
US04334097

Reaction notes

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