Imidazole → 2-[4-(tert-Butyldimethylsilyoxy)phenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrile

HRID 392966Notes

Reaction equation

HRID 392966 reaction equation
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:24]3[CH:32]=[CH:33][C:34]([C:36]#[N:37])=[CH:35][C:23]=3[N:22]=2)=[CH:17][CH:16]=1>CN(C=O)C>[Si:10]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[C:24]3[CH:32]=[CH:33][C:34]([C:36]#[N:37])=[CH:35][C:23]=3[N:22]=2)=[CH:17][CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1356740912-[4-Hydroxyphenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrile

Product 1

HCID 226608142-[4-(tert-Butyldimethylsilyoxy)phenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (2.72 g, 0.040 mol) and tert-butyldimethylchloro silane (2.89 g, 192 mmol) were added to a stirred solution of compound 6 (5.1 g, 16 mmol) in DMF (10 mL). Stirring was continued for 15 h at 100° C. Upon cooling 20 crystallized. The crystals were collected and washed with ethyl acetate followed by water. The yield of 20 (after drying) was 4.70 g (62%).

Workup

  1. temperatureUpon cooling 20
  2. customcrystallized
  3. customThe crystals were collected
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-bfe9783747a1445697440d5e4bd45f3a
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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