Imidazole → HCID 10760398, compound

HRID 2299017Notes

Reaction equation

HRID 2299017 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[CH:9]1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>>[F:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH2:13][O:14][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[N:10]=[CH:9]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10585933[1-(2-Fluoro-4-nitrophenyl)-1H-imidazol-4-yl]methanol

Product 1

HCID 10760398HCID 10760398, compound

Procedure

3-Fluoro-4-(4-hydroxymethylimidazol-1-yl)nitrobenzene (26.7 g) and imidazole (15.3 g) were suspended in dry N,N-dimethylformnamide (190 ml) and stirred under argon on an ice-bath. t-Butyldimethylsilylchloride (25.5 g) was added in one portion, and stirring continued at ice temperature for 30 minutes, then at ambient temperature overnight. Solvent was evaporated in vacuo at 30° C., the residue diluted with water (200 ml) and extracted into ethyl acetate (700 ml). After washing with water (2×300 ml), brine, and drying over magnesium sulfate, solvent was evaporated (finally on high vacuum) to give an oil which solidified (39.2 g). This was used in the next stage with no further purification.

Workup

  1. stirringstirring
  2. customat ambient temperature
  3. customovernight
  4. customSolvent was evaporated in vacuo at 30° C.
  5. additionthe residue diluted with water (200 ml)
  6. extractionextracted into ethyl acetate (700 ml)
  7. washAfter washing with water (2×300 ml), brine
  8. dry with materialdrying over magnesium sulfate, solvent
  9. customwas evaporated (finally on high vacuum)
  10. customto give an oil which
  11. customThis was used in the next stage with no further purification

Sources & evidence

ORD record
ord-58f2879112654cf7a11b0c5b5e466555
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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