4-Toluenesulfonyl chloride → HCID 86750013, compound

HRID 1901307Notes

Reaction equation

HRID 1901307 reaction equation
[F:1][P-:2]([F:7])([F:6])([F:5])([F:4])[F:3].[C:8]1([CH3:27])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S+:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC(S(Cl)(=O)=[O:35])=CC=1.[O-][O-].[Na+].[Na+]>C(#N)C.O>[F:1][P-:2]([F:7])([F:6])([F:5])([F:4])[F:3].[C:8]1([CH3:27])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S+:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:35]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14803Sodium peroxideHCID 23133109HCID 23133109, compound

Product 1

HCID 86750013HCID 86750013, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(Tolyl)diphenylsulphonium hexafluorophosphate (1.08 g, 2.57 mmol) is dissolved with stirring in acetonitrile (40 ml). The resulting solution is stirred while p-toluene- sulphonyl chloride (2.38 g, 12.5 mmol) added. The reaction mixture is cooled in an ice-water bath. A solution of sodium peroxide (2.42 g, 31 mmol) in water (30 ml) is added dropwise over 20 minutes. After a further 2 hours the reaction mixture is filtered under vacuum and the filtrate evaporated in vacuo. Water is added and the resulting solid collected, and washed with water and ether to give (tolyl)diphenylsulphoxonium hexafluorophosphate (0.63 g, 56%) with spectra identical to authentic material.

Workup

  1. additionadded
  2. temperatureThe reaction mixture is cooled in an ice-water bath
  3. filtrationAfter a further 2 hours the reaction mixture is filtered under vacuum
  4. customthe filtrate evaporated in vacuo
  5. additionWater is added
  6. customthe resulting solid collected
  7. washwashed with water and ether

Sources & evidence

ORD record
ord-2959d5072c76491fae0e17b83c9a4598
Source dataset
uspto-grants-1996_11
Patent number
US05576461

Reaction notes

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