Acetic Anhydride → 2-Methyl-N-propylprop-2-enamide

HRID 968041Notes

Reaction equation

HRID 968041 reaction equation
Cl.NCCC[CH:6]=[C:7]([CH3:11])[C:8]([NH2:10])=[O:9].C(O[C:16](=O)[CH3:17])(=O)C.[CH2:19](N(CC)CC)C.C([NH-])(=O)C>CO>[CH3:19][CH2:16][CH2:17][NH:10][C:8](=[O:9])[C:7]([CH3:11])=[CH2:6]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21947001AcetimidateHCID 866009693-Aminopropyl methacrylamide hydrochloride

Product 1

HCID 97937652-Methyl-N-propylprop-2-enamideYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.8 g of 3-aminopropyl methacrylamide hydrochloride was dissolved in a methanol solvent and 0.9 g of acetic anhydride and 0.9 g of triethylamine (TEA) were added thereto. The resultant mixture was stirred under ice-cooling for 4 hours. After the completion of the reaction, the solvent was distilled off with an evaporator and the precipitate was filtered off. The filtrate was recovered and introduced into a silica column. Thus, the eluate fraction containing the target product was taken up and subjected to recrystallization to thereby purify the target acetylamide, N-3-propyl methacrylamide (yield: 92%).

Workup

  1. additionwere added
  2. temperaturecooling for 4 hours
  3. customAfter the completion of the reaction
  4. distillationthe solvent was distilled off with an evaporator
  5. filtrationthe precipitate was filtered off
  6. customThe filtrate was recovered
  7. additionintroduced into a silica column
  8. additionThus, the eluate fraction containing the target product
  9. customsubjected to recrystallization

Sources & evidence

ORD record
ord-ef9454bd0e574f18b49a30f89cd8c813
Source dataset
uspto-grants-2005_10
Patent number
US06956077B1

Reaction notes

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