Benzyl Chloride → HCID 66627682, compound

HRID 1471267Notes

Reaction equation

HRID 1471267 reaction equation
[CH2:1]([C:11]1[NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[N:12]=1)[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH2:1]([C:2]1[N:6]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1)[C:11]1[N:12]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1

Participants

5

Reactant 3

HCID 7503Benzyl Chloride2×HCID 11430Potassium CarbonateHCID 2609682,2'-methylenebis(1h-benzimidazole)

Product 1

HCID 66627682HCID 66627682, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 2.0 g 2,2′-methylenebis(1H-benzimidazole), 2.8 g potassium carbonate, 100 ml N,N-dimethylformamide and the mixture was stirred under nitrogen. 2.5 g benzyl chloride were added and the mixture was heated to 70 C for 16 hours. Another 0.7 g benzyl chloride was added and the reaction was heated to 70 C for another 20 hours. The reaction was cooled to 22 C, quenched with 150 ml water and the product was extracted with ethyl acetate and washed with water. Following removal of solvent, the product was recrystallized from 10 ml ethanol, then 10 ml acetonitrile with 1 ml of water. The product was filtered and dried resulting in 0.67 g tan solid.

Workup

  1. temperaturethe mixture was heated to 70 C for 16 hours
  2. temperaturethe reaction was heated to 70 C for another 20 hours
  3. temperatureThe reaction was cooled to 22 C
  4. customquenched with 150 ml water
  5. extractionthe product was extracted with ethyl acetate
  6. washwashed with water
  7. customremoval of solvent
  8. customthe product was recrystallized from 10 ml ethanol
  9. filtrationThe product was filtered
  10. customdried

Sources & evidence

ORD record
ord-36904f90ccd04aeda8b14dc3f6bca2a3
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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