Dimethyl Sulfate → N-alpha-methoxyethyl-N-methyl-acetamide

HRID 2059121Notes

Reaction equation

HRID 2059121 reaction equation
S(OC)(O[CH3:5])(=O)=O.[OH-].[Na+].[CH3:10][O:11][CH:12]([NH:14][C:15](=[O:17])[CH3:16])[CH3:13]>N>[CH3:10][O:11][CH:12]([N:14]([CH3:5])[C:15](=[O:17])[CH3:16])[CH3:13]

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 14798Sodium HydroxideHCID 10986197N-(1-methoxyethyl)acetamide

Product 1

HCID 21464473N-alpha-methoxyethyl-N-methyl-acetamideYield 457.4%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

25 g (0.2 mole) of dimethyl sulfate are added to 500 ml of 50% strength sodium hydroxide solution at 5°-10° C., and 158 g (1.25 moles) of dimethyl sulfate and 117 g (1.0 mole) of N-α-methoxyethyl-acetamide are simultaneously added dropwise in the course of 3 hours, while stirring. After a further 3 hours, 50 ml of concentrated ammonia are added, and after 30 minutes, the phases are separated in a separating funnel and the aqueous layer is extracted with diethyl ether. After stripping off the solvent, distillation of the residue in vacuo gives 120 g (92% of theory) of N-α-methoxyethyl-N-methyl-acetamide of boiling point18 76°-81° C.

Workup

  1. waitafter 30 minutes
  2. customthe phases are separated in a separating funnel
  3. extractionthe aqueous layer is extracted with diethyl ether
  4. distillationthe solvent, distillation of the residue in vacuo

Sources & evidence

ORD record
ord-e6348200394a40779bacefbc88537e8d
Source dataset
uspto-grants-1982_03
Patent number
US04322271

Reaction notes

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