Dimethyl Sulfate → N-(Dimethoxymethyl)-N-ethylethanamine

HRID 1283578Notes

Reaction equation

HRID 1283578 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[CH2:8]([N:10]([CH2:13][CH3:14])[CH:11]=[O:12])[CH3:9].[CH3:15][O-].[Na+]>CO>[N:10]([CH:11]([O:6][CH3:7])[O:12][CH3:15])([CH2:13][CH3:14])[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 12051DiethylformamideHCID 10942334Sodium Methoxide

Product 1

HCID 12747026N-(Dimethoxymethyl)-N-ethylethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

985 g of dimethyl sulfate were added to 790 g (7.8 moles) of N,N-diethylformamide while stirring, in the course of which the internal temperature rose to 40°C. After the batch had been stirred overnight, the mixture was allowed to run into 7.8 moles of sodium methylate in methanol (total volume approximately 2.3 l) at 0° to 5°C, while stirring, and the reaction mixture was again stirred overnight. The methanol was then distilled from the crystal paste. The desired product was subsequently distilled off up to a bath temperature of 170°C under 10 mm Hg, and was then fractionally distilled through a column. 862 g (75% of theory) of N,N-diethylformamide-dimethylacetal of boiling point 70°C/50 mm Hg (foaming) and of refractive index nD24 of 1.4074 were obtained.

Workup

  1. customrose to 40°C
  2. stirringAfter the batch had been stirred overnight
  3. stirringwhile stirring
  4. distillationThe methanol was then distilled from the crystal paste
  5. distillationThe desired product was subsequently distilled off up to a bath temperature of 170°C under 10 mm Hg
  6. distillationwas then fractionally distilled through a column
  7. customof 1.4074 were obtained

Sources & evidence

ORD record
ord-c776323a57f14c009585925ee22b7c54
Source dataset
uspto-grants-1976_08
Patent number
US03975523

Reaction notes

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