Imidazole → HCID 67286620, compound

HRID 1045331Notes

Reaction equation

HRID 1045331 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[OH:14][C:15]1[CH:24]=[CH:23][C:18]2[S:19][C:20](=[O:22])[O:21][C:17]=2[CH:16]=1.O>CN(C)C=O>[Si:10]([O:14][C:15]1[CH:24]=[CH:23][C:18]2[S:19][C:20](=[O:22])[O:21][C:17]=2[CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 721396-Hydroxy-1,3-benzoxathiol-2-one

Product 1

HCID 67286620HCID 67286620, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (972 mg) and t-butylchlorodimethylsilane (2.15 g) were added to a solution of 6-hydroxy-1,3-benzoxathiol-2-one (2.00 g) in N,N-dimethylformamide (60 mL) to form a reaction solution. This reaction solution was stirred for 4 hours at normal temperature. Water was added to the reaction solution, and the reaction solution was extracted with ethyl acetate. The extract was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain the target product (3.00 g) as a colorless oil.

Workup

  1. customto form a reaction solution
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe anhydrous sodium sulfate was removed by filtration
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-ea92a6f6e7014d8e8bf4f6a01d8b3523
Source dataset
uspto-grants-2013_10
Patent number
US08569270B2

Reaction notes

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