Potassium Carbonate → HCID 6481624, compound

HRID 1072014Notes

Reaction equation

HRID 1072014 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:27][C:28]([NH:30][CH3:31])=[O:29]>CN(C)C=O>[N:11]1([CH2:10][C:2]2[N:1]([CH2:27][C:28]([NH:30][CH3:31])=[O:29])[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 667732-chloro-N-methylacetamideHCID 3822419HCID 3822419, compound

Product 1

HCID 6481624HCID 6481624, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(1H-Benzimidazol-2-ylmethyl)-1H-benzotriazole (500 mg, 2.00 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 mL). Potassium carbonate (1.11 g, 8.00 mmol) and 2-chloro-N-methylacetamide (237 mg, 2.20 mmol) were added. The reaction mixture was allowed to stir overnight at reflux. The solvent was evaporated under vacuum, and the white waxy residue taken up in methylene chloride (300 mL). The organic extract was washed with saturated aqueous sodium bicarbonate (2×100 mL), dried over magnesium sulfate, filtered and evaporated. The residue was purified by chromatography (CH2Cl2/MeOH=15:1) to give 304 mg (47%) of the title compound as a white solid.

Workup

  1. temperatureat reflux
  2. customThe solvent was evaporated under vacuum
  3. extractionThe organic extract
  4. washwas washed with saturated aqueous sodium bicarbonate (2×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (CH2Cl2/MeOH=15:1)

Sources & evidence

ORD record
ord-dcc2264433cb4c77bfbfcb1b55c7854d
Source dataset
uspto-grants-2005_06
Patent number
US06908936B2

Reaction notes

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