Imidazole → HCID 70945116, compound

HRID 332622Notes

Reaction equation

HRID 332622 reaction equation
OC[C:3]1[S:7][CH:6]=[N:5][CH:4]=1.N1C=CN=[CH:9]1.C(N(C(C)C)CC)(C)C.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].[OH2:30]>CN(C)C=O.C(OCC)(=O)C>[Si:22]([O:30][C:3]1[S:7][C:6]([CH3:9])=[N:5][CH:4]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 27632165-Thiazolylmethanol

Product 1

HCID 70945116HCID 70945116, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Hydroxymethylthiazole (5.0 g, 43 mmol), imidazole (7.4 g, 109 mmol), and diisopropylethylamine (14 g, 109 mmol) were dissolved in N,N-dimethylformamide (50 mL), tert-butyldimethylsilyl chloride (13.1 g, 87 mmol) was added, and the mixture was stirred at room temperature for 20 hours. Ethyl acetate (200 mL) and water (100 mL) were added to the reaction mixture, the mixture was partitioned, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and purified by silica gel column chromatography to give the title compound.

Workup

  1. customthe mixture was partitioned
  2. washthe organic layer was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a19b2873245c4e95bc9038ccfee5a8eb
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

Loading…