Water → 6-Bromo-1-[(4-nitrophenyl)sulfonyl]-1H-benzimidazole

HRID 520601Notes

Reaction equation

HRID 520601 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14].O>CN(C=O)C.C(Cl)Cl.CO.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][N:8]([S:22]([C:19]3[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=3)(=[O:23])=[O:24])[C:4]=2[CH:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178419331HCID 178419331, compound

Product 1

HCID 682265396-Bromo-1-[(4-nitrophenyl)sulfonyl]-1H-benzimidazole

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-1H-benzimidazole (756 mg) was dissolved in anhydrous DMF (3 ml) and cooled in an ice bath. Sodium hydride (60% in mineral oil) (153 mg) was added in one portion. The reaction was stirred for 1 h, before addition of 4-nitrobenzenesulfonyl chloride (850 mg) in DMF (2 ml) to the reaction. The reaction was stirred for a further hour before warming to RT and addition of water (10 ml). The reaction was stirred vigorously then left at RT overnight. Ethyl acetate (ca. 10 ml) was added to the reaction mixture and was then vigorously stirred. The reaction was dissolved in DCM:methanol and passed through a 1 g SAX cartridge. The residue was purified on silica cartridge using cyclohexane:ethyl acetate with a 50-100% gradient. Fractions containing the product were combined and evaporated to dryness to afford the title compound, 401 mg.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe reaction was stirred vigorously
  3. stirringwas then vigorously stirred
  4. customThe residue was purified on silica cartridge
  5. additionFractions containing the product
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a790b5d1add349c591519a28b8ccaa7c
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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