Acetic Acid → HCID 67370923, compound

HRID 1375372Notes

Reaction equation

HRID 1375372 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[C:6]1[I:16])[CH2:2][CH2:3][CH3:4].[C:17](O)(=[O:19])C.C([O-])(=O)C.[Na+]>C=O.O>[CH2:1]([N:5]1[C:9]([CH2:17][OH:19])=[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:7][CH:6]1[I:16])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 18437784HCID 18437784, compound

Product 1

HCID 67370923HCID 67370923, compound

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 962WaterSolvent

Procedure

1-Butyl-2-iodo-4-phenyl-1H-imidazole (3.26 g) is dissolved in formaldehyde (16.1 mL). Acetyl alcohol (5.5 mL) and sodium acetate (20 g) are added to the solution and the mixture is refluxed under N2 for 4 hours. The reaction mixture is diluted with H2O, adjusted to pH 9, extracted with ethyl acetate, and dried over Na2SO4. Concentration and purification of the extract via flash chromatography yields (1-butyl-2-iodo-4-phenyl-3H-imidazol-5-yl)-methanol.

Workup

  1. temperaturethe mixture is refluxed under N2 for 4 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration and purification of the
  5. extractionextract via flash chromatography

Sources & evidence

ORD record
ord-61ee7d4c8596452e9c8171bdc5fffb11
Source dataset
uspto-grants-2007_01
Patent number
US07169775B2

Reaction notes

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