Acetic Acid → 2-Iodo-1-triphenylmethylimidazole-4-carboxylic acid

HRID 1108277Notes

Reaction equation

HRID 1108277 reaction equation
[I:1][C:2]1[N:3]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=[C:5]([C:7]([O:9]C)=[O:8])[N:6]=1.C(O)(=O)C>[OH-].[Na+].C(OCC)(=O)C>[I:1][C:2]1[N:3]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 187846292-Iodo-4-(methoxycarbonyl)-1-triphenylmethylimidazole

Product 1

HCID 187846222-Iodo-1-triphenylmethylimidazole-4-carboxylic acidYield 87%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 2-iodo-4-(methoxycarbonyl)-1-triphenylmethylimidazole (1.978 g, 4 mmol) in 6N sodium hydroxide (15 mL) was heated at reflux for 4 hours. The resulting suspension was diluted with ethyl acetate (20 mL) and then slightly acidified with acetic acid. The resulting clear solution was extracted three times with ethyl acetate (20 mL) and the combined extracts were dried (magnesium sulfate) and concentrated in vacuo. Residual acetic acid was removed under high vacuum to give 2-iodo-1-triphenylmethylimidazole-4-carboxylic acid (1.67 g, 87%) as a white solid, mp 203-205° C.: 1H NMR (CDCl3) δ 7.60 (s, 1H), 7.38-7.20 (m, 9H), 7.18-7.09 (m, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. extractionThe resulting clear solution was extracted three times with ethyl acetate (20 mL)
  4. dry with materialthe combined extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. customResidual acetic acid was removed under high vacuum

Sources & evidence

ORD record
ord-38dccbc51e5f4004ba82d8989d029d56
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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