Water → 2-Methyl-N-(2-methylbutan-2-yl)prop-2-enamide

HRID 1608004Notes

Reaction equation

HRID 1608004 reaction equation
[CH3:1][C:2](=[CH:4][CH3:5])[CH3:3].[C:6](#[N:10])[C:7]([CH3:9])=[CH2:8].S(=O)(=O)(O)[OH:12].O>C(O)(=O)C>[CH3:1][C:2]([NH:10][C:6](=[O:12])[C:7]([CH3:9])=[CH2:8])([CH2:4][CH3:5])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 105532-Methyl-2-buteneHCID 31368Methacrylonitrile

Product 1

HCID 146180182-Methyl-N-(2-methylbutan-2-yl)prop-2-enamideYield 65.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Methyl-2-butene (7.0 g) was added to a stirred mixture of methacrylonitrile (6.7 g) in acetic acid (50 ml) and concentrated sulfuric acid (10 g) at 10° to 20° C. The mixture was allowed to stand overnight at room temperature, and then poured into 200 g of water and extracted with methylene chloride (2×100 ml). The methylene chloride solution was dried over sodium sulfate, the solid filtered off and the methylene chloride evaporated to afford an oily product. Distillation of the product at 10 mm yielded N-(2-methyl-2-butyl)methacrylamide (10.1 g, 65%); bp 84° C.

Workup

  1. extractionextracted with methylene chloride (2×100 ml)
  2. dry with materialThe methylene chloride solution was dried over sodium sulfate
  3. filtrationthe solid filtered off
  4. customthe methylene chloride evaporated
  5. customto afford an oily product
  6. distillationDistillation of the product at 10 mm

Sources & evidence

ORD record
ord-a79b999e6d39437c8f1e607cf426637d
Source dataset
uspto-grants-1989_09
Patent number
US04868310

Reaction notes

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