Potassium Carbonate → HCID 178433284, compound

HRID 1635942Notes

Reaction equation

HRID 1635942 reaction equation
Cl.[CH3:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[CH2:8][OH:9].[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Si:14]([O:9][CH2:8][C:7]1[NH:6][CH:5]=[N:4][C:3]=1[CH3:2])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 178433279HCID 178433279, compound

Product 1

HCID 178433284HCID 178433284, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

13.0 g(87.5 mmol) of 4-methyl-5-imidazolemethanol hydrochloride, 13.5 g(89.6 mmol) of t-butylchlorodimethylsilane and 14.5 g(105 mmol) of potassium carbonate were added to 200 ml of dimethylformamide and the resulting mixture was stirred for 3 days. After dimethylformamide was removed under reduced pressure, 500 ml of ethylacetate was added to the residue which was then washed with aqueous sodium chloride solution (200 ml×3). The organic layer was dried over anhydrous magnesium sulfate and concentrated to give 5.4 g(23.9 mmol, Yield 27%) of the title compound.

Workup

  1. customAfter dimethylformamide was removed under reduced pressure, 500 ml of ethylacetate
  2. additionwas added to the residue which
  3. washwas then washed with aqueous sodium chloride solution (200 ml×3)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6b4d757a460444cb8039e012e231a791
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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