Dimethylformamide → Dimethyl Sulfate

HRID 1076275Notes

Reaction equation

HRID 1076275 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 three 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-8ddd1074c7274e7ba8354ba2627861fc
Source dataset
uspto-grants-1976_05
Patent number
US03956354

Reaction notes

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