Potassium Carbonate → HCID 68183782, compound

HRID 878978Notes

Reaction equation

HRID 878978 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH2:22]Cl>CN(C)C=O>[CH3:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH2:22][N:3]1[C:4]2[CH:9]=[C:8]([C:10]([O:12][CH2:22][C:21]3[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:20]=3[CH3:19])=[O:11])[CH:7]=[CH:6][C:5]=2[N:1]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 4594565-Benzimidazolecarboxylic acid

Product 1

HCID 68183782HCID 68183782, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-benzoimidazole carboxylic acid (1.1 g) in N,N-dimethylformamide (15 mL) were added potassium carbonate (2.7 g) and 2,6-dimethylbenzyl chloride (2.3 g) at room temperature, and then the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was quenched with water, and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (1.1 g) as a white solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with chloroform
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dc7c68cae8394e23b93b64d33e4eff5b
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

Loading…