Diisopropylethylamine → [1-(2-Fluoro-4-nitrophenyl)-1H-imidazol-4-yl]methanol

HRID 2299016Notes

Reaction equation

HRID 2299016 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[OH:12][CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:17]1[CH:18]=[C:14]([CH2:13][OH:12])[N:15]=[CH:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 178519868HCID 178519868, compound

Product 1

HCID 10585933[1-(2-Fluoro-4-nitrophenyl)-1H-imidazol-4-yl]methanolYield 75.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,4-Difluoro-nitrobenzene (23.85 g) was dissolved in acetonitrile (180 ml), followed by 4-hydroxymethylimidazole (14.7 g) and ethyldiisopropylamine (65.2 ml). The mixture was stirred and heated to reflux for 2 days. After cooling, acetonitrile was evaporated and the residue was shaken with a mixture of methyl t-butyl ether (200 ml) and water (100 ml), and the solid filtered. After washing with a mixture of methyl t-butyl ether (50 ml) and water (25 ml), the solid was dried in vacuo at 60° C. overnight, to give product (26.8 g) mp 157-159° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 days
  3. temperatureAfter cooling
  4. customacetonitrile was evaporated
  5. stirringthe residue was shaken with a mixture of methyl t-butyl ether (200 ml) and water (100 ml)
  6. filtrationthe solid filtered
  7. washAfter washing with a mixture of methyl t-butyl ether (50 ml) and water (25 ml)
  8. customthe solid was dried in vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-fabc34a3a9434a34886752a8d5307204
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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