Imidazole → HCID 86655663, compound

HRID 2047464Notes

Reaction equation

HRID 2047464 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([NH:13][CH2:14][CH2:15][OH:16])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.N1C=CN=C1.[C:24]([Si:28]([CH3:31])([CH3:30])Cl)([CH3:27])([CH3:26])[CH3:25].O>CC(N(C)C)=O>[Si:28]([O:16][CH2:15][CH2:14][NH:13][C:5]1[CH:4]=[C:3]([C:2]([F:17])([F:18])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:6]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 201299412-[3,5-Bis(trifluoromethyl)anilino]ethan-1-ol

Product 1

HCID 86655663HCID 86655663, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of the compound (0.38 g) obtained in step 1, imidazole (0.12 g) and tert-butyldimethylchlorosilane (0.26 g) in DMAc (5 mL) was stirred at room temperature for 14 hr, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous ammonium chloride solution and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 3→10% ethyl acetate/hexane) to give N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3,5-bis(trifluoromethyl)aniline (0.48 g, 89%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous ammonium chloride solution and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (solvent gradient; 3→10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6337652b9a884d92a820c11c05b11e65
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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