Imidazole → HCID 15769668, compound

HRID 2393097Notes

Reaction equation

HRID 2393097 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C)C=O.O>[Si:13]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 132242-Methyl-8-hydroxyquinolineHCID 28928tert-Butyldimethylsilyl chloride2×

Product 1

HCID 15769668HCID 15769668, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8-Hydroxyquinaldine (10 g), t-butyldimethylsilyl chloride (10 g) and imidazole (8.6 g) were dissolved in N,N-dimethylformamide (150 ml) and stirred at ambient temperature overnight. Further t-butyldimethylsilyl chloride (4.7 g) was added and the reaction stirred for another 30 minutes. The reaction was diluted with water (600 ml) and extracted with dichloromethane (3×300 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo to afford the title compound as an orange oil (17 g).

Workup

  1. stirringthe reaction stirred for another 30 minutes
  2. extractionextracted with dichloromethane (3×300 ml)
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b78f5aa54304ade89271e856f0aaaad
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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