Imidazole → 3-((Tert-butyldimethylsilyl)oxy)aniline

HRID 2175377Notes

Reaction equation

HRID 2175377 reaction equation
Cl[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[NH2:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.N1C=CN=C1>ClCCl>[Si:2]([O:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[NH2:9])([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 115683-AminophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 143147823-((Tert-butyldimethylsilyl)oxy)anilineYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloro t-butyldimethylsilane (11 g, 72.98 mmol), 3-aminophenol (6.64 g, 60.81 mmol) and imidazole (5.38 g, 79.10 mmol) were added into 200 ml of dichloromethane. The mixture was stirred at room temperature for 15 hours. The reaction mixture was extracted using 200 ml of saturated ammonium chloride and 200 m of dichloromethane and the organic layer was washed twice using 200 ml of water. After concentrated under vacuum, the title compound (13.5 g, 99%) was obtained.

Workup

  1. extractionThe reaction mixture was extracted
  2. washthe organic layer was washed twice
  3. concentrationAfter concentrated under vacuum

Sources & evidence

ORD record
ord-52985dd9a7a342a6b72dda2793ef43e9
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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