Potassium Carbonate → HCID 178433283, compound

HRID 1635938Notes

Reaction equation

HRID 1635938 reaction equation
Cl.[CH3:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[CH2:8][OH:9].C(=O)([O-])[O-].[K+].[K+].[Si:16](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ClCCl.CO>CN(C)C=O>[Si:16]([O:9][CH2:8][C:7]1[NH:6][CH:5]=[N:4][C:3]=1[CH3:2])([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 94078tert-ButyldiphenylchlorosilaneHCID 21226129Dichloromethane methanolHCID 178433279HCID 178433279, compound

Product 1

HCID 178433283HCID 178433283, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2.0 g(13.5 mmol) of 4-methyl-5-imidazolemethanol hydrochloride and 1.95 g(14.17 mmol) of potassium carbonate in 20 ml of dimethylformamide was added 3.88 g(14.17 mmol) of t-butyldiphenylsilylchloride was added dropwise thereto, and the resulting mixture was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was dissolved in 20 ml of ethylacetate. The organic layer was washed with 20 ml of saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to column chromatography(eluent: dichloromethane/methanol=95/5, v/v) to give 1.22 g(3.44 mmol, Yield 26%) of the title compound.

Workup

  1. additionwas added dropwise
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in 20 ml of ethylacetate
  4. washThe organic layer was washed with 20 ml of saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-149f533c48734598b4ca80be11246eb7
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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