Phosphorus pentachloride → (3-Cyanophenyl)methanesulfonyl chloride

HRID 2204060Notes

Reaction equation

HRID 2204060 reaction equation
[Na+].[C:2]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH2:7][S:8]([O-])(=[O:10])=[O:9])#[N:3].P(Cl)(Cl)(Cl)(Cl)[Cl:16]>P(Cl)(Cl)(Cl)=O>[C:2]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH2:7][S:8]([Cl:16])(=[O:10])=[O:9])#[N:3]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 23684849HCID 23684849, compound

Product 1

HCID 16774314(3-Cyanophenyl)methanesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
80 °C

Procedure

5 g (22.83 mmol) of 3-cyanobenzylsulfonic acid sodium salt were moistened with approx. 20 ml of phosphoryl chloride, after which 5.2 g (25.11 mmol) of PCl5 were added and the mixture was stirred for 15 min while being cooled with ice. The mixture was then heated at 80° C. for 4 h. After that, the mixture was poured onto ice and stirred vigorously for 30 min in connection with which the product sedimented as a white solid on the ice. After the ice had been partially thawed, the mixture was filtered through a frit and the product/ice mixture which remained was washed several times with water. The crystals which remained were dried in vacuo and used directly for the next step in the synthesis.

Workup

  1. temperaturewhile being cooled with ice
  2. additionAfter that, the mixture was poured onto ice
  3. stirringstirred vigorously for 30 min in connection with which the product
  4. filtrationthe mixture was filtered through a frit
  5. washthe product/ice mixture which remained was washed several times with water
  6. customThe crystals which remained were dried in vacuo
  7. customused directly for the next step in the synthesis

Sources & evidence

ORD record
ord-6ebcb2b45c424436b86e687d03f4250a
Source dataset
uspto-grants-2016_06
Patent number
US09365613B2

Reaction notes

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