Imidazole → 4-[(tert-butyldimethylsilyl)oxy]-N-phenylaniline

HRID 518926Notes

Reaction equation

HRID 518926 reaction equation
[NH:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21].O>C(#N)C>[Si:24]([O:14][C:11]1[CH:10]=[CH:9][C:8]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:12]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 312084-Hydroxydiphenylamine

Product 1

HCID 917415864-[(tert-butyldimethylsilyl)oxy]-N-phenylaniline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 12 g of 4-anilinophenol (64.7 mmol) in 200 mL of acetonitrile there are added, at ambient temperature, 6.7 g of imidazole (97.05 mmol) and 11.7 g of tert-butyl(chloro)dimethylsilane (77.64 mmol). The batch is stirred at 70° C. for 4 hours. The reaction mixture is then poured into water and extracted with ether. The organic phase is then dried over magnesium sulphate, then filtered and evaporated to dryness. The crude product thereby obtained is then purified by chromatography over silica gel (petroleum ether/dichloromethane gradient). The title product is obtained in the form of a powder.

Workup

  1. extractionextracted with ether
  2. dry with materialThe organic phase is then dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product thereby obtained
  6. customis then purified by chromatography over silica gel (petroleum ether/dichloromethane gradient)

Sources & evidence

ORD record
ord-38cd0277e98c48ea9bd94c47b89a9275
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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