Nitric Acid → HCID 3691019, compound

HRID 1356659Notes

Reaction equation

HRID 1356659 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([NH:6][S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[N+:19]([O-])([OH:21])=[O:20].O>C(O)(=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([NH:6][S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[C:4]([N+:19]([O-:21])=[O:20])[CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 76182Benzenesulfonamide, N-(4-chlorophenyl)-4-methyl-

Product 1

HCID 3691019HCID 3691019, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 4′-chloro-p-toluenesulfonanilide (1100 g (3.90 mol) in acetic acid (2200 ml), fuming nitric acid (273.9 g (4.22 mol) was added dropwise over a period of 40 minutes with stirring at 50° C. After completion of the addition, the reaction mixture was stirred at the same temperature to complete the reaction. After being left to cool to room temperature, the reaction mixture was treated with 7000 ml of water to bring about precipitation of crystals. The crystals were filtered and washed with water to give 1261 g (99%) of 4′-chloro-2′-nitro-p-toluenesulfonanilide as yellow crystals.

Workup

  1. additionAfter completion of the addition
  2. stirringthe reaction mixture was stirred at the same temperature
  3. customthe reaction
  4. waitAfter being left
  5. temperatureto cool to room temperature
  6. customto bring about precipitation of crystals
  7. filtrationThe crystals were filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-a12651615337428183f96b24e4eaddbf
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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