Phosphorus oxychloride → 2',4'-Dicyano-p-toluenesulfonanilide

HRID 1356653Notes

Reaction equation

HRID 1356653 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:9]1[CH:25]=[C:24]([C:26](=O)[NH2:27])[CH:23]=[CH:22][C:10]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])(=O)[NH2:7]>O>[C:6]([C:9]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:10]=1[NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)(=[O:14])=[O:13])#[N:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18509262HCID 18509262, compound

Product 1

HCID 185093212',4'-Dicyano-p-toluenesulfonanilideYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Phosphorus oxychloride (5.00 g) was added to 2′,4′-dicarbamoyl-p-toluenesulfonanilide (0.30 g (0.90 mmol), and the mixture was heated at 50° C. for 4 hours with stirring. After cooling, addition of water, and stirring brought about precipitation of an insoluble solid. These crystals were filtered, washed with water and recrystallized from ethyl acetate-hexane to give 0.16 g (60%) of 2′,4′-dicyano-p-toluenesulfonanilide as pale brown crystals.

Workup

  1. temperatureAfter cooling
  2. stirringstirring
  3. custombrought about precipitation of an insoluble solid
  4. filtrationThese crystals were filtered
  5. washwashed with water
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ba6d7025796645d0b29ddd3b82254cb3
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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