Sodium Bicarbonate → HCID 178432730, compound

HRID 216318Notes

Reaction equation

HRID 216318 reaction equation
[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][C:4]1[N:5]=[C:6]([CH3:10])[N:7](O)[CH:8]=1.C(=O)(O)[O-].[Na+]>CO.[Cl-].[Ti+3].[Cl-].[Cl-]>[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][C:4]1[N:5]=[C:6]([CH3:10])[NH:7][CH:8]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 686676414-(2,2-dimethylpropyl)-2-methyl-1H-imidazol-1-ol

Product 1

HCID 178432730HCID 178432730, compound

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolvent

Procedure

Titanium (III) chloride (30% weight solution in 2N HCl) (600 mL, 1.5 mol) was added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-methyl-1H-imidazol-1-ol (ca. 0.56 mmol) in methanol (1200 mL). After stirring at ambient temperature for a few days, the reaction mixture was basified with saturated aqueous sodium bicarbonate until the black solution turned white. The reaction mixture was extracted with ether. The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 10-20% ethyl acetate/hexane afforded 4-(2,2-dimethylpropyl)-2-methyl-1H-imidazole.

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-322421c136d749628ace9adadd934aeb
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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