Butanal, oxime → 1-Hydroxy-4,5-dimethyl-3-oxido-2-propylimidazol-3-ium

HRID 917947Notes

Reaction equation

HRID 917947 reaction equation
[CH:1](=[N:5][OH:6])[CH2:2][CH2:3][CH3:4].[CH3:7]/[C:8](/[C:11]([CH3:13])=O)=[N:9]\[OH:10]>CCOCC>[CH3:13][C:11]1[N+:5]([O-:6])=[C:1]([CH2:2][CH2:3][CH3:4])[N:9]([OH:10])[C:8]=1[CH3:7]

Participants

4

Reactant 2

HCID 8069Butanal, oximeHCID 64096332,3-Butanedione monoxime

Product 1

HCID 3286061-Hydroxy-4,5-dimethyl-3-oxido-2-propylimidazol-3-ium

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of butyraldoxime (8.7 g., 0.1 mole) and diacetyl monoxime (10.1 g., 0.1 mole) was warmed to obtain a homogeneous solution. After standing for 2 days at room-temperature, the mixture was heated on the steam-bath for 3 hr., and then diluted with ether (500 ml), the tan solid separated was removed by filtration (16.7 g.) and recrystallised from ethanol (95%) having a melting point 174°-175°C

Workup

  1. temperaturewas warmed
  2. customto obtain a homogeneous solution
  3. temperaturethe mixture was heated on the steam-bath for 3 hr
  4. customthe tan solid separated
  5. customwas removed by filtration (16.7 g.)
  6. customrecrystallised from ethanol (95%)

Sources & evidence

ORD record
ord-963622a8a1564f68a42ad6a510bba7c4
Source dataset
uspto-grants-1976_07
Patent number
US03968220

Reaction notes

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