Lithium iodide → HCID 70132244, compound

HRID 429619Notes

Reaction equation

HRID 429619 reaction equation
[O:1]([CH2:19][C:20]1[NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([O:31]C)=[O:30])[C:22]=2[N:21]=1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[I-].[Li+]>N1C=CC=CC=1>[O:1]([CH2:19][C:20]1[NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([OH:31])=[O:30])[C:22]=2[N:21]=1)[Si:2]([C:15]([CH3:18])([CH3:16])[CH3:17])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 70104971HCID 70104971, compound

Product 1

HCID 70132244HCID 70132244, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 2-tert-butyldiphenylsiloxymethyl-1H-benzimidazole-4-carboxylate (500 mg) in pyridine (3 ml) was added lithium iodide (602 mg) under nitrogen at ambient temperature and the mixture was heated to reflux for 3 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in chloroform. The solution was washed with water and brine and the organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (chloroform only˜50:1˜25:1˜10:1) to give 2-tert-butyldiphenylsiloxymethyl-1H-benzimidazole-4-carboxylic acid (425 mg) as a powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe solution was washed with water and brine
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (chloroform only˜50:1˜25:1˜10:1)

Sources & evidence

ORD record
ord-043b641715644842b0e8b9c2ea96e65c
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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