Methyl Acrylate → methyl 3-(N-vinylformamido)propionate

HRID 2211303

Reaction equation

HRID 2211303 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH:7]([NH:9][CH:10]=[O:11])=[CH2:8]>C1(=O)C=CC(=O)C=C1.C[O-].[Na+]>[CH:7]([N:9]([CH2:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[CH:10]=[O:11])=[CH2:8]

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 83191N-Vinylformamide

Product 1

HCID 10964771methyl 3-(N-vinylformamido)propionateYield 92%

Reagents, catalysts & solvents 2

HCID 4650QuinoneCatalystHCID 10942334Sodium MethoxideCatalyst

Procedure

To a 1000 mL three-neck round bottom flask equipped with a cold water condenser and stirrer was added 215 grams (2.5 moles) of methyl acrylate, 195 grams (2.75 moles) of N-vinylformamide, and 0.1 gram of benzoquinone. The mixture was stirred at ambient temperature for two minutes and 1.5 grams of sodium methoxide was added in one portion. The mixture was stirred for approximately 2 hours at ambient temperature and allowed to stand overnight. The reaction mixture was distilled under vacuum and 361 grams of product (92% yield) boiling at 75° C. (0.8 mm Hg) was collected for analysis. 1H NMR analysis confirmed the identity of the 3-(N-vinylformamido) adduct.

Workup

  1. customTo a 1000 mL three-neck round bottom flask equipped with a cold water condenser and stirrer
  2. stirringThe mixture was stirred for approximately 2 hours at ambient temperature
  3. waitto stand overnight

Sources & evidence

ORD record
ord-4de949084264410b84638d23eb6b1d12
Source dataset
uspto-grants-1995_10
Patent number
US05463110

Linked notes

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