Potassium Carbonate → HCID 6481624, compound

HRID 1796124Notes

Reaction equation

HRID 1796124 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-e1a9c422c7c341c1ac7c5788a9b9b88f
Source dataset
uspto-grants-2006_04
Patent number
US07030140B2

Reaction notes

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