4-Nitrobenzenesulfonyl chloride → HCID 20300031, compound

HRID 1733707Notes

Reaction equation

HRID 1733707 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1)([O-:13])=[O:12]>[OH-].[Na+].C(OCC)(=O)C>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([S:20]([O:1][N:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N:4]=[N:3]2)(=[O:22])=[O:21])=[CH:18][CH:19]=1)([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 20300031HCID 20300031, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

In 1 N aqueous sodium hydroxide (b 98 ml) is dissolved 1-hydroxy-1,2,3-benzotriazole (13.5 g). To the solution is added powdery p-nitrobenzenesulfonyl chloride (22.2 g) with stirring under ice-cooling, and the mixture is stirred at the same temperature for 15 minutes and further at room temperature for 4.5 hours. After allowing to stand overnight, the reaction mixture is extracted with ethyl acetate (150 ml). The extract is washed with water and dried over anhydrous sodium sulfate. After drying, the solvent is distilled off. The resulting powdery residue is washed twice with petroleum ether (30 ml) and recrystallized from benzene (90 ml) to give colorless crystals. The crystals are dissolved in ethyl acetate (100 ml) and the mixture is washed twice with a saturated aqueous sodium hydrogen carbonate (10 ml) and water in order and dried over anhydrous sodium sulfate. After drying, the solvent is distilled off under a reduced pressure to give colorless crystals of 1-(p-nitrobenzensulfonyloxy)-1,2,3-benzotriazole (14 g), melting point: 119.5°-121.5° C. Ultraviolet spectrum (methanol): λmax 254 nm, E=234.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at the same temperature for 15 minutes and further at room temperature for 4.5 hours
  3. extractionthe reaction mixture is extracted with ethyl acetate (150 ml)
  4. washThe extract is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter drying
  7. distillationthe solvent is distilled off
  8. washThe resulting powdery residue is washed twice with petroleum ether (30 ml)
  9. customrecrystallized from benzene (90 ml)
  10. customto give colorless crystals
  11. washthe mixture is washed twice with a saturated aqueous sodium hydrogen carbonate (10 ml) and water in order
  12. dry with materialdried over anhydrous sodium sulfate
  13. customAfter drying
  14. distillationthe solvent is distilled off under a reduced pressure

Sources & evidence

ORD record
ord-0c245d8e2276436998f1f73b2bfba6f0
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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