Nitric Acid → 4'-Cyano-2'-nitro-p-toluenesulfonanilide

HRID 1356665Notes

Reaction equation

HRID 1356665 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:5][CH:4]=1)#[N:2].[N+:20]([O-])([OH:22])=[O:21].O>C(OC(=O)C)(=O)C>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 962WaterHCID 257975n-(4-Cyanophenyl)-4-methylbenzenesulfonamide

Product 1

HCID 107342434'-Cyano-2'-nitro-p-toluenesulfonanilideYield 97%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a suspension of 4′-cyano-p-toluenesulfonanilide (1153 g (4.23 mol) in acetic anhydride (2306 ml), fuming nitric acid (294.3 g (4.53 mol) was added dropwise, keeping the temperature at 50° C. with stirring, over a period of 100 minutes. After completion of the addition, the reaction mixture was stirred at 50° C. for 1.5 hours. Then, 1.75 ml (0.042 mol) of fuming nitric acid was further added and stirring was continued for another one hour at 50° C. To the resulting mixture, after being left to cool to room temperature, water (7000 ml) was then added to make crystals to deposite. After stirring under cooling with ice for one hour, the crystals were filtered and washed with water to give 1305 g (97%) of 4′-cyano-2′-nitro-p-toluenesulfonanilide as yellow crystals.

Workup

  1. customat 50° C.
  2. additionAfter completion of the addition
  3. stirringthe reaction mixture was stirred at 50° C. for 1.5 hours
  4. stirringstirring
  5. waitwas continued for another one hour at 50° C
  6. waitTo the resulting mixture, after being left
  7. stirringAfter stirring
  8. temperatureunder cooling with ice for one hour
  9. filtrationthe crystals were filtered
  10. washwashed with water

Sources & evidence

ORD record
ord-751ee58a596a4478a8ba7547d8364e9f
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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