Methanol → N,N-diallyl-O-methylisourea

HRID 329003Notes

Reaction equation

HRID 329003 reaction equation
[CH2:1]([N:4]([CH2:7][CH:8]=[CH2:9])[C:5]#[N:6])[CH:2]=[CH2:3].[C-]#N.[K+].[CH3:13][OH:14]>O>[CH2:1]([N:4]([CH2:7][CH:8]=[CH2:9])[C:5](=[NH:6])[O:14][CH3:13])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 9032Potassium CyanideHCID 10849Cyanamide, diallyl

Product 1

HCID 21440852N,N-diallyl-O-methylisoureaYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The following reactants were combined in a 1-liter, round-bottom flask: 24.4 g (0.2 mole) diallylcyanamide, 13 g (0.2 mole) KCN and 500 ml methanol. The mixture was heated under reflux for 24 hours, then stripped in vacuo. The residue was dissolved in 250 ml H2O, which was subsequently extracted with three 200 ml portions of diethyl ether. The organic phases were combined, washed with 200 ml of H2O and dried with MgSO4. The solvent was evaporated to yield 20.7 g (67% yield) of N,N-diallyl-O-methylisourea.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. extractionwhich was subsequently extracted with three 200 ml portions of diethyl ether
  4. washwashed with 200 ml of H2O
  5. dry with materialdried with MgSO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8a9a2033eb344c8d83de7db8b243bb0e
Source dataset
uspto-grants-1977_04
Patent number
US04018917

Reaction notes

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