Imidazole → HCID 11551990, compound

HRID 1295462Notes

Reaction equation

HRID 1295462 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.N1C=CN=C1.[C:15]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16]>CN(C)C=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:21])[CH3:20])=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1437134-Iodo-2-methylphenol

Product 1

HCID 11551990HCID 11551990, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Iodo-2-methylphenol (15.0 g, 64.1 mmol) was dissolved in N,N-dimethylformamide (250 ml), and imidazole (8.7 g, 128.2 mmol, 2.0 eq.) added to the mixture, tert-Butyldimethyl silyl chloride (10.6 g, 70.5 mmol, 1.1 eq.) was slowly added to the above mixture and stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was extracted with aqueous ammonium chloride solution and ethyl acetate, and dried over magnesium sulfate. The crude product was purified on silica flash column. The solvent was evaporated under reduced pressure to thereby yield 21.8 g of the title compound (yield: 97.5%).

Workup

  1. additionwas slowly added to the above mixture
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with aqueous ammonium chloride solution and ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was purified on silica flash column

Sources & evidence

ORD record
ord-3e55025ac2a348bda294dc910404d443
Source dataset
uspto-grants-2007_07
Patent number
US07241901B2

Reaction notes

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