Imidazole → Clioquinol, o-(tert-butyldimethylsilyl)-

HRID 2301429Notes

Reaction equation

HRID 2301429 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([I:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].N1C=CN=C1>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([I:12])[C:9]([O:13][Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 2788ClioquinolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 632411Clioquinol, o-(tert-butyldimethylsilyl)-Yield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flame-dried, 50-mL, three-necked flask is charged with 5-chloro-8-hydroxy-7-iodoquinoline (2.814 g), which is commercially available, t-butyldimethylchlorosilane (1.76 g), and 10 mL of DMF. Imidazole (1.66 g) is added, and the resulting mixture is stirred at room temperature for 18 h. The reaction mixture is then quenched with 10 mL of saturated aqueous NaHCO3 and extracted with hexane three times. The combined organic layers are dried over MgSO4, filtered and concentrated to give 3.898 g of the title compound as a pale green solid.

Workup

  1. customThe reaction mixture is then quenched with 10 mL of saturated aqueous NaHCO3
  2. extractionextracted with hexane three times
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-da5fabcf4d9b4477b4afa60598ad9b24
Source dataset
uspto-grants-2002_12
Patent number
US06500842B1

Reaction notes

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