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

HRID 2272874Notes

Reaction equation

HRID 2272874 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]>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

5

Reactant 3

HCID 795ImidazoleHCID 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 whole is stirred at 70° C. for 4 hours. Then the reaction mixture is poured onto water and extracted with ether. The organic phase is subsequently dried over magnesium sulphate and then filtered and evaporated to dryness. The crude product so 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. additionThen the reaction mixture is poured onto water
  2. extractionextracted with ether
  3. dry with materialThe organic phase is subsequently dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product so obtained
  7. customis then purified by chromatography over silica gel (petroleum ether/dichloromethane gradient)

Sources & evidence

ORD record
ord-edca8ab8877c4e4ab290ed85435d8919
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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