Methanol → Methyl 2-acrylamido-2-methylpropanesulfonate

HRID 1657512Notes

Reaction equation

HRID 1657512 reaction equation
[OH:1][S:2](O)(=O)=[O:3].[O:6]=S(=O)=O.[C:10](#[N:13])[CH:11]=[CH2:12].[CH2:14]=[C:15]([CH3:17])[CH3:16].CO.COC1C=C[C:25]([OH:28])=CC=1>>[C:10]([NH:13][C:15]([CH3:17])([CH3:16])[CH2:14][S:2]([O:28][CH3:25])(=[O:3])=[O:1])(=[O:6])[CH:11]=[CH2:12]

Participants

6

Reactant 5

HCID 887MethanolHCID 7855Acrylonitrile2×HCID 8255Isobutylene2×HCID 90154-MethoxyphenolHCID 24681Fuming sulfuric acid3×

Product 1

HCID 19088270Methyl 2-acrylamido-2-methylpropanesulfonate

Procedure

Following substantially the procedure of Example 1, a reaction mixture is prepared from 400.3 grams (4.45 gramatoms of sulfur) of 40% oleum, 1930 grams (36.4 moles) of acrylonitrile (containing 0.013% water) and 56 grams (1 equivalent) of isobutene. The addition rates are the same as in Example 1 except that the oleum addition rate is 6.8 grams per minute. Following the completion of the acrylonitrile and isobutene addition, oleum addition is continued until the indicated amount has been introduced. The reaction mixture is then poured into 128 grams (4 moles) of methanol at 5°-10°C., over one hour. p-Methoxyphenol, 0.5 gram, is added as a polymerization inhibitor and the solution is poured over 1000 grams of ice. The organic layer is separated; the aqueous layer is washed with aqueous sodium sulfate solution and extracted with three 500-ml. portions of chloroform. The organic layer and chloroform extracts are dried over magnesium sulfate and the volatile materials are stripped to yield the desired methyl 2-acrylamido-2-methylpropanesulfonate which is recrystallized from a benzene-cyclohexane mixture. The recrystallized product melts at 78°-81°C.

Workup

  1. additionThe addition rates
  2. additionhas been introduced
  3. customThe organic layer is separated
  4. washthe aqueous layer is washed with aqueous sodium sulfate solution
  5. extractionextracted with three 500-ml
  6. dry with materialThe organic layer and chloroform extracts are dried over magnesium sulfate

Sources & evidence

ORD record
ord-a4ae0d621a3a4030b0d3074854d34e6a
Source dataset
uspto-grants-1976_06
Patent number
US03960918

Reaction notes

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