Phenylmethanesulfonyl chloride → HCID 20300035, compound

HRID 1733694Notes

Reaction equation

HRID 1733694 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.[CH2:12]([S:19](Cl)(=[O:21])=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[OH-].[Na+].O.CCOCC>[CH2:12]([S:19]([O: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)(=[O:21])=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 2327116-Chloro-1-hydroxy-1H-benzotriazole

Product 1

HCID 20300035HCID 20300035, compoundYield 56.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

In 1 N aqueous sodium hydroxide (13.0 ml) and water is dissolved 1-hydroxy-6-chloro-1,2,3-benzotriazole (2.23 g) and thereto is added dropwise a solution of benzylsulfonyl chloride (2.5 g) in ether (50 ml) under ice-cooling and stirring, and the mixture is stirred at the same temperature for 1.5 hours and further at room temperature for 1 hour. The reaction mixture is distilled to remove ether. To the resulting residue is added ethyl acetate. The ethyl acetate layer is dried and distilled to remove the solvent. The residue is recrystallized from benzene-n-hexane to give white needles of 1-benzylsulfonyloxy-6-chloro-1,2,3-benzotriazole (2.4 g), melting point: 126.5°-127.5° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at the same temperature for 1.5 hours and further at room temperature for 1 hour
  3. distillationThe reaction mixture is distilled
  4. customto remove ether
  5. additionTo the resulting residue is added ethyl acetate
  6. dry with materialThe ethyl acetate layer is dried
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-2bbd2f5d491a477e895b20f26d3133e0
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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