5-Nitrobenzimidazole → HCID 18373205, compound

HRID 842371Notes

Reaction equation

HRID 842371 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C1COCC1.O>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]([S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH:9]=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 71955-NitrobenzimidazoleHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 18373205HCID 18373205, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 5-nitrobenzimidazole (7.5 g, 46 mmol) in THF (300 mL) and water (150 mL) was added K2CO3 (15.9 g, 115 mmol), followed by p-toluenesulfonyl chloride (11.4 g, 46 mmol). After stirring for 16 h, solvents were removed in vacuo and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic phase was washed with brine, then dried with MgSO4, filtered and concentrated in vacuo. The crude solid was dissolved in choloroform and chromatographed over a silica gel column with a gradient of chloroform through 10% methanol/chloroform. The product containing fractions were combined and concentrated in vacuo to give 11.4 g (79%) of light yellow solid.

Workup

  1. customsolvents were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe crude solid was dissolved in choloroform
  9. customchromatographed over a silica gel column with a gradient of chloroform through 10% methanol/chloroform
  10. additionThe product containing fractions
  11. concentrationconcentrated in vacuo
  12. customto give 11.4 g (79%) of light yellow solid

Sources & evidence

ORD record
ord-10a8a96555f84d3190c8867d2528d780
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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