Water → N,N-Di(prop-2-en-1-yl)acetamide

HRID 477579Notes

Reaction equation

HRID 477579 reaction equation
Cl.[CH2:2]([NH:5][CH2:6][CH:7]=[CH2:8])[CH:3]=[CH2:4].[C:9](OC(=O)C)(=[O:11])[CH3:10].O>N1C=CC=CC=1>[C:9]([N:5]([CH2:6][CH:7]=[CH2:8])[CH2:2][CH:3]=[CH2:4])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 521977Diallylamine hydrochloride

Product 1

HCID 241027N,N-Di(prop-2-en-1-yl)acetamideYield 90.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 10 ml of pyridine was dissolved 0.5 g of diallylamine hydrochloride, and 1.0 g of acetic anhydride was added to the solution. The mixture was stirred at room temperature for 10 hours. Water was added to the mixture and the mixture was extracted with chloroform. The chloroform layer was washed with 0.01 N aqueous HCl solution, 1% aqueous sodium bicarbonate solution and finally with water, and concentrated to obtain 0.47 g of N-acetyldiallylamine [IR: 1640 cm-1, 1H-NMR δH 2.08 (3H), 3.94(4H), 5.16(4H), 5.76(2H)].

Workup

  1. additionwas added to the solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was washed with 0.01 N aqueous HCl solution, 1% aqueous sodium bicarbonate solution and finally with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4bc326eb77224024b96c97af07723e50
Source dataset
uspto-grants-1989_12
Patent number
US04888418

Reaction notes

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