HCID 21950481, compound → 2-(Methanesulfonyl)benzonitrile

HRID 1288266Notes

Reaction equation

HRID 1288266 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=O)(=[O:4])=[O:3]>P(Cl)(Cl)(Cl)=O>[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]#[N:9])(=[O:3])=[O:4]

Participants

3

Reactant 1

HCID 21950481HCID 21950481, compound

Product 1

HCID 223462902-(Methanesulfonyl)benzonitrileYield 87.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

2-Methanesulphonylbenzamide (34 g.) was added to phosphorus oxychloride (100 ml.) and the mixture was refluxed for 90 minutes. The excess of phosphorus oxychloride was evaporated in vacuo, and the oily residue was treated with water (200 ml.), with ice cooling. The solid which separated was filtered off, washed with water and recrystallised from ethanol to give 2-methanesulphonylbenzonitrile (27 g.), m.p. 105°-106° C.

Workup

  1. temperaturethe mixture was refluxed for 90 minutes
  2. customThe excess of phosphorus oxychloride was evaporated in vacuo
  3. additionthe oily residue was treated with water (200 ml.), with ice cooling
  4. customThe solid which separated
  5. filtrationwas filtered off
  6. washwashed with water
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-394b98742ce743418c8da40afff7a674
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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