4-Toluenesulfonyl chloride → HCID 86750013, compound

HRID 1901308Notes

Reaction equation

HRID 1901308 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+]>ClCCl.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 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

(Tolyl)diphenylsulphonium hexafluorophosphate (1.08 g, 2.57 mmol) and p-toluenesulphonyl chloride (2.38 g, 12.5 mmol) are dissolved with stirring in dichloromethane (40 ml), with cooling in ice-water. A solution of sodium peroxide (2.42 g, 31 mmol) in water (30 ml) is added dropwise over 20 minutes. After further stirring overnight the reaction mixture is diluted with dichloromethane and water. The mixture is allowed to separate and the dichloromethane containing layer collected, dried over magnesium sulphate, filtered and evaporated in vacuo. The resulting solid is slurried in water and collected. It is further washed with water and ether to yield (tolyl)diphenylsulphoxonium hexafluorophosphate (0.73 g, 65%) identical to authentic material.

Workup

  1. customto separate
  2. customthe dichloromethane containing layer collected
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customcollected
  7. washIt is further washed with water and ether

Sources & evidence

ORD record
ord-1720071296ab4c2e8bf1460ecd32f5f1
Source dataset
uspto-grants-1996_11
Patent number
US05576461

Reaction notes

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