Hydrochloric Acid → (4-Nitrophenyl)[2-(1-propyl)imidazolyl]methanol

HRID 856780Notes

Reaction equation

HRID 856780 reaction equation
C([N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)CC.[N+:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1)([O-:11])=[O:10].Cl.C(=O)([O-])[O-].[K+].[K+].[CH2:27]1[CH2:31]OC[CH2:28]1>CCCCCC.C([Li])CCC>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([CH:16]([C:7]2[N:6]=[C:5]([CH2:28][CH2:27][CH3:31])[NH:4][CH:8]=2)[OH:17])=[CH:18][CH:19]=1)([O-:11])=[O:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 8028Tetrahydrofuran2×HCID 11430Potassium CarbonateHCID 118785n-Propylimidazole

Product 1

HCID 178440139(4-Nitrophenyl)[2-(1-propyl)imidazolyl]methanol

Reagents, catalysts & solvents 1

HCID 178418244HCID 178418244, compoundSolvent

Procedure

To a solution of 1-propylimidazole (8.0 g) in dry THF (100 ml), 1.6M n-butyllithium hexane solution (54.5 ml) was at 0° C. under argon atmosphere. After the mixture was allowed to be at room temperature and was stirred for 2 hours, a solution of 4-nitrobenzaldehyde (9.97 g) in dry THF (100 ml) was added dropwise to the mixture at −78° C. The mixture was allowed to be at room temperature and was stirred overnight, and then, 1N hydrochloric acid was added to the mixture at 0° C. The mixture was neutralized with potassium carbonate, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was recrystallized from ethyl acetate-diisopropyl ether, to give (4-nitrophenyl)[2-(1-propyl)imidazolyl]methanol (5.26 g) as brown crystals.

Workup

  1. customwas at 0° C. under argon atmosphere
  2. customto be at room temperature
  3. customto be at room temperature
  4. stirringwas stirred overnight
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe obtained residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-36bc0a96fab649c2baf5e41377a30342
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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