Imidazole → HCID 69733417, compound

HRID 412423Notes

Reaction equation

HRID 412423 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]([F:14])([F:13])[F:12])=[C:6]([CH2:8][OH:9])[CH:7]=1.N1[CH:19]=[CH:18]N=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C=O)C>[Si:20]([O:9][CH2:8][C:6]1[CH:7]=[C:2]([NH:1][C:19]2[CH:18]=[CH:6][CH:7]=[CH:2][CH:3]=2)[CH:3]=[CH:4][C:5]=1[O:10][C:11]([F:12])([F:13])[F:14])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22311140(5-Amino-2-trifluoromethoxy-phenyl)-methanol

Product 1

HCID 69733417HCID 69733417, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(5-Amino-2-trifluoromethoxyphenyl)methanol (1.2 g, 5.8 mmol) was dissolved in DMF (5 mL) and imidazole (0.48 g, 7.1 mmol) and tert-butyldimethylsilylchloride (0.99 g, 6.6 mmol) were added and the mixture was stirred for 16 hours. The reaction mixture was extracted with ethyl acetate (50 mL) and water (20 mL). The aqueous phase was extracted once more with ethyl acetate (20 mL). The combined organic phases were washed with water (10 mL), aqueous citric acid (10 mL, 10%) and water (2×10 mL), dried (magnesium sulphate) and concentrated in vacuo. The residue was purified by column chromatography (110 g, silica gel) using ethyl acetate and heptane (1:3) as eluent to give 1.2 g of 3-(tert-butyldimethylsilanyloxymethyl)-4-trifluoromethoxyphenylaniline.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (50 mL) and water (20 mL)
  2. extractionThe aqueous phase was extracted once more with ethyl acetate (20 mL)
  3. washThe combined organic phases were washed with water (10 mL), aqueous citric acid (10 mL, 10%) and water (2×10 mL)
  4. dry with materialdried (magnesium sulphate)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (110 g, silica gel)

Sources & evidence

ORD record
ord-91596dc104374c2e82c64d2ccbc26318
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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