Dimethylformamide → Dimethyl Sulfate

HRID 1578532Notes

Reaction equation

HRID 1578532 reaction equation
[CH3:1]N(C)[CH:3]=[O:4].[C:6]([NH:10][C:11]([CH3:18])([CH3:17])[CH2:12][S:13]([O-:16])(=[O:15])=[O:14])(=[O:9])[CH:7]=[CH2:8].[Na+].[CH3:20]OC1C=CC(O)=CC=1>C1C=CC=CC=1>[S:13]([O:4][CH3:3])([O:16][CH3:20])(=[O:14])=[O:15].[C:6]([NH:10][C:11]([CH3:18])([CH3:17])[CH2:12][S:13]([O:16][CH3:1])(=[O:14])=[O:15])(=[O:9])[CH:7]=[CH2:8]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 90154-MethoxyphenolHCID 236657192-Acrylamido-2-methylpropanesulphonate sodium salt

Product 2

HCID 6497Dimethyl SulfateHCID 19088270Methyl 2-acrylamido-2-methylpropanesulfonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

An addition product of dimethyl sulfate and dimethylformamide is prepared according to the method of Example 3. To 0.5 mole of this product is added a mixture of 59 grams (0.25 mole) of sodium 2-acrylamido-2-methylpropanesulfonate, 0.1 gram of p-methoxyphenol and 500 ml. of benzene. The mixture is heated under reflux, with stirring, for 3 hours, after which the benzene is evaporated under vacuum. The remaining solid is recrystallized from a benzene-cyclohexane mixture to yield the desired methyl 2-acrylamido-2-methylpropanesulfonate.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux
  3. customafter which the benzene is evaporated under vacuum
  4. customThe remaining solid is recrystallized from a benzene-cyclohexane mixture

Sources & evidence

ORD record
ord-bf534bd5a60b4bef8494fbdba455fd8f
Source dataset
uspto-grants-1976_02
Patent number
US03937721

Reaction notes

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