Imidazole → 4-Chloro-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenylpropyl]amino]benzonitrile

HRID 966959Notes

Reaction equation

HRID 966959 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([NH:10][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13][OH:14])[CH:3]=1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>O1CCCC1.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([NH:10][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13][O:14][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 222939464-Chloro-2-[(3-hydroxy-1-phenylpropyl)amino]benzonitrile

Product 1

HCID 222939214-Chloro-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenylpropyl]amino]benzonitrileYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-2-[(3-hydroxy-1-phenylpropyl)amino]benzonitrile (2.3 g, 8 mmol) in dry tetrahydrofuran (50 ml) was treated with tert-butyldimethylsilylchloride (2.41 g, 2 eq.) and imidazole (1.09 g, 2 eq.) and stirred at room temperature for 1 h. The reaction mixture was diluted with water (200 ml) and the products extracted into diethyl ether (200 ml). The organic extract was dried over magnesium sulphate and concentrated to an oil. The crude product was purified on silica gel eluting with isohexane/diethyl ether (2:1) to afford the title compound as a colourless oil (2.3 g, 72%).

Workup

  1. extractionthe products extracted into diethyl ether (200 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulphate
  4. concentrationconcentrated to an oil
  5. customThe crude product was purified on silica gel eluting with isohexane/diethyl ether (2:1)

Sources & evidence

ORD record
ord-e4c2b0efa9ed41318e47be748549c423
Source dataset
uspto-grants-2005_10
Patent number
US06953797B2

Reaction notes

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