Water → HCID 561404, compound

HRID 1356655Notes

Reaction equation

HRID 1356655 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.O>N1C=CC=CC=1>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17])#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 729132-Aminobenzonitrile

Product 1

HCID 561404HCID 561404, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-aminobenzonitrile (2.36 g (20.0 mmol in pyridine (10.0 ml), p-toluenesulfonyl chloride (4.20 g (22.0 mmol) was added with stirring at room temperature. After 15 hours' stirring at room temperature, water (100 ml) was added to the reaction mixture and stirring was continued for another 30 minutes. The crystals separated were filtered, washed with water and re-dissolved in chloroform. The soluble part in 1% aqueous sodium hydroxide solution was extracted from the chloroform solution. The extract was made acidic with hydrochloric acid and re-extracted with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a product which then crystallized. The crystals were washed with diisopropyl ether and filtered to give 4.83 g (89%) of 2′-cyano-p-toluenesulfonanilide as white crystals.

Workup

  1. stirringAfter 15 hours' stirring at room temperature
  2. stirringstirring
  3. customThe crystals separated
  4. filtrationwere filtered
  5. washwashed with water
  6. dissolutionre-dissolved in chloroform
  7. extractionThe soluble part in 1% aqueous sodium hydroxide solution was extracted from the chloroform solution
  8. extractionre-extracted with chloroform
  9. extractionThe chloroform extract
  10. dry with materialwas dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customto give a product which
  13. customthen crystallized
  14. washThe crystals were washed with diisopropyl ether
  15. filtrationfiltered

Sources & evidence

ORD record
ord-3106eca8ddd9436f8efe310954ae431c
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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