Butyric anhydride → 2-Methyl-N-propylprop-2-enamide

HRID 968042Notes

Reaction equation

HRID 968042 reaction equation
Cl.NCCC[CH:6]=[C:7]([CH3:11])[C:8]([NH2:10])=[O:9].[C:12](OC(=O)CCC)(=O)[CH2:13][CH2:14]C.C(N(CC)CC)C.C([NH-])(=O)CCC>CO>[CH3:12][CH2:13][CH2:14][NH:10][C:8](=[O:9])[C:7]([CH3:11])=[CH2:6]

Participants

6

Reactant 4

HCID 7798Butyric anhydrideHCID 8471TriethylamineHCID 866009693-Aminopropyl methacrylamide hydrochlorideHCID 178449865Butyrylamide

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 1.5 g of butyric 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 butyrylamide, 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-928b4b374f5f43269c4b0ee1a5cdf949
Source dataset
uspto-grants-2005_10
Patent number
US06956077B1

Reaction notes

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