2-Chlorobenzaldehyde → 1H-Imidazole, 1-hydroxy-4,5-dimethyl-2-phenyl-

HRID 528057Notes

Reaction equation

HRID 528057 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10]/[C:11](/[C:14]([CH3:16])=O)=[N:12]\[OH:13].O.[NH3:18]>CCO>[CH3:16][C:14]1[N:18]=[C:4]([C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:2]=2)[N:12]([OH:13])[C:11]=1[CH3:10]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 64096332,3-Butanedione monoxime2×HCID 12896473Azane;hydrate

Product 1

HCID 51303471H-Imidazole, 1-hydroxy-4,5-dimethyl-2-phenyl-Yield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Chlorobenzaldehyde (160 mmol) was added to a suspended solution of 2,3-butanedione monoxime (240 mmol) in EtOH. After stirring for 30 minutes, 2,3-butanedione monoxime (240 mmol) and 112 mL of 28% ammonia water were added. The reaction mixture was stirred for 12 hours at room temperature. The mixture was concentrated under reduced pressure and the residue was diluted with methylene chloride. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel with an eluent of 5% MeOH in CH2Cl2 gave 19.3 g (64%) of 4,5-dimethyl-2-phenyl-1H-imidazol-1-ol as a white solid.

Workup

  1. stirringThe reaction mixture was stirred for 12 hours at room temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with methylene chloride
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography on silica gel with an eluent of 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-9d105b046eae436991bd1a93797380d7
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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