Diethyl Ether → 1-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole

HRID 1733701Notes

Reaction equation

HRID 1733701 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.CCOCC.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>[OH-].[Na+]>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:1][N:2]2[C:6]3[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=3[N:4]=[N:3]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 73984-Chlorobenzenesulfonyl chlorideHCID 2327116-Chloro-1-hydroxy-1H-benzotriazole

Product 1

HCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazoleYield 91.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 1 N aqueous sodium hydroxide (300 ml) is dissolved 1-hydroxy-6-chloro-1,2,3-benzotriazole (38 g) and thereto is added ether (100 ml). To the solution is added dropwise p-chlorobenzenesulfonyl chloride (57 g) with stirring under ice-cooling during 15 minutes, and the mixture is stirred at the same temperature for 70 minutes. The reaction mixture is extracted with ethyl acetate. The extract is washed with a saturated aqueous sodium hydrogen carbonate and water in order and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off, and the resulting crystals are recrystallized from benzene-petroleum ether to give 1-(p-chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole (70.5 g), melting point: 125°-127° C. Infrared spectrum (Nujor): 1190, 1085 cm-1.

Workup

  1. temperaturecooling during 15 minutes
  2. stirringthe mixture is stirred at the same temperature for 70 minutes
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. washThe extract is washed with a saturated aqueous sodium hydrogen carbonate and water in order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter drying
  7. distillationthe solvent is distilled off
  8. customthe resulting crystals are recrystallized from benzene-petroleum ether

Sources & evidence

ORD record
ord-a5c4dc6ca4654aee821b9439a9fe0492
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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