Nitric Acid → HCID 178440153, compound

HRID 1249557Notes

Reaction equation

HRID 1249557 reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[C:6]([C:15]([C:21]([F:24])([F:23])[F:22])([C:17]([F:20])([F:19])[F:18])[OH:16])[NH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:3].[N+:25]([O-])([OH:27])=[O:26]>O>[CH3:3][CH:2]([C:4]1[N:5]=[C:6]([C:15]([C:21]([F:24])([F:22])[F:23])([C:17]([F:18])([F:19])[F:20])[OH:16])[NH:7][C:8]=1[C:9]1[CH:10]=[CH:11][C:12]([N+:25]([O-:27])=[O:26])=[CH:13][CH:14]=1)[CH3:1]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178440152HCID 178440152, compound

Product 1

HCID 178440153HCID 178440153, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4-(1-methylethyl)-5-phenyl-α,α-bis(trifluoromethyl)-1H-imidazole-2-methanol (1.75 g) in 40 ml of water was added 2.5 ml of concentrated nitric acid in a dropwise manner. The mixture was stirred for 30 minutes, and the nitrate salt, 1.51 g) was filtered off. The solid in 5 ml of concentrated sulfuric acid was heated at reflux for 2 hours. The reaction mixture was poured into 50 ml of ice-water. The mixture was basified to a pH of 8 and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness to afford a yellow solid which was purified by flash chromatography on silica gel (85:15 hexane/ethyl acetate) to afford (0.98 g, 50%) of the title compound as a pale yellow solid, m.p. 157°-160° C.

Workup

  1. filtrationthe nitrate salt, 1.51 g) was filtered off
  2. temperatureThe solid in 5 ml of concentrated sulfuric acid was heated
  3. temperatureat reflux for 2 hours
  4. additionThe reaction mixture was poured into 50 ml of ice-water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customto afford a yellow solid which
  11. customwas purified by flash chromatography on silica gel (85:15 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4e8344c5b8954a1ab8bf76d9d1fd3574
Source dataset
uspto-grants-1986_12
Patent number
US04632930

Reaction notes

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