Methanol → Methyl 2-acrylamido-2-methylpropanesulfonate

HRID 1657513Notes

Reaction equation

HRID 1657513 reaction equation
[C:1]([NH:5][C:6]([CH3:13])([CH3:12])[CH2:7][S:8]([OH:11])(=[O:10])=[O:9])(=[O:4])[CH:2]=[CH2:3].[CH3:14]O>OS(O)(=O)=O.O=S(=O)=O>[C:1]([NH:5][C:6]([CH3:13])([CH3:12])[CH2:7][S:8]([O:11][CH3:14])(=[O:9])=[O:10])(=[O:4])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 653602-Acrylamido-2-methyl-1-propanesulfonic acid

Product 1

HCID 19088270Methyl 2-acrylamido-2-methylpropanesulfonate

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent2×

Procedure

A 25-gram portion of 65% oleum (containing 0.203 mole of sulfur trioxide) is poured over 20 grams (0.097 equivalent) of 2-acrylamido-2-methylpropanesulfonic acid. The mixture warms as the acid dissolves in the oleum. The viscous mixture is stirred for 10 minutes and is then poured into 300 ml. (7.42 equivalents) of methanol, while the vessel containing the latter is cooled with ice. After the mixture becomes homogeneous it is stripped to about 100 ml. and extracted with chloroform. The chloroform extracts are combined and dried over sodium sulfate, and the desired methyl 2-acrylamido-2-methylpropanesulfonate is obtained upon stripping the chloroform.

Workup

  1. additionis then poured into 300 ml
  2. temperaturelatter is cooled with ice
  3. extractionand extracted with chloroform
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-f1a1d3abb5e44cef8866b379370cef27
Source dataset
uspto-grants-1976_06
Patent number
US03960918

Reaction notes

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