Phosphorus pentachloride → (4-Nitrophenyl)methanesulfonyl chloride

HRID 1647777Notes

Reaction equation

HRID 1647777 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([O-])(=[O:11])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:17]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([Cl:17])(=[O:11])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 5314401Sodium (4-nitrophenyl)methanesulfonate

Product 1

HCID 2794642(4-Nitrophenyl)methanesulfonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 28.3 g (118 mmol, 1.0 equiv.) of finely ground sodium 4-nitrobenzyl sulfonate in 250 mL of toluene was added 24.6 g (118 mmol, 1.0 equiv) of finely ground phosphorous pentachloride as the solid in portions. After addition the mixture was heated to reflux for one hour. The mixture was cooled, and volatile material was removed in vacuo. The residue was dissolved in 500 mL chloroform and 250 mL of water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give 27.8 g (100%) of 4-nitrobenzyl sulfonyl chloride, pure by 1H NMR.

Workup

  1. additionAfter addition the mixture
  2. temperaturewas heated
  3. temperatureto reflux for one hour
  4. temperatureThe mixture was cooled
  5. customvolatile material was removed in vacuo
  6. dissolutionThe residue was dissolved in 500 mL chloroform
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9efdb4aa89144c87bc3d1091325edec1
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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