Phosphorus pentachloride → (4-Cyanophenyl)methanesulfonyl chloride

HRID 1952988Notes

Reaction equation

HRID 1952988 reaction equation
[Na].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([OH:14])(=O)=[O:12])=[CH:6][CH:5]=1)#[N:3].P(Cl)(Cl)(Cl)(Cl)[Cl:16]>C(#N)C>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([Cl:16])(=[O:14])=[O:12])=[CH:6][CH:5]=1)#[N:3]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 5360545SodiumHCID 12801688HCID 12801688, compound

Product 1

HCID 15480555(4-Cyanophenyl)methanesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1.1 g (5.02 mMol) of the sodium salt of 4-cyanobenzenemethanesulphonic acid in 20 ml of acetonitrile was mixed with 1.2 g (5.76 mMol) of phosphorus-(V)-chloride and then refluxed for 24 hours. The insoluble matter was filtered off and the filtrate was evaporated down in vacuo. Yield; 0.8 g (74% of theory). The product was used in the next step without purification.

Workup

  1. temperaturerefluxed for 24 hours
  2. filtrationThe insoluble matter was filtered off
  3. customthe filtrate was evaporated down in vacuo
  4. customThe product was used in the next step without purification

Sources & evidence

ORD record
ord-a5e0cd29cb304df0be7bd304719ca75e
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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