Hydrochloric Acid → 4-Acetylamino-3,5-bis-trifluoromethylbenzenesulfonamide

HRID 1288311Notes

Reaction equation

HRID 1288311 reaction equation
[C:1]([NH:4][C:5]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:8](N)=[CH:7][C:6]=1[C:16]([F:19])([F:18])[F:17])(=[O:3])[CH3:2].Cl.[N+:21]([O-])([O-])=O.[Na+].[S:26](=[O:28])=[O:27]>C(O)(=O)C.O>[C:1]([NH:4][C:5]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:8]([S:26]([NH2:21])(=[O:28])=[O:27])=[CH:7][C:6]=1[C:16]([F:19])([F:18])[F:17])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur Dioxide2×HCID 24268Sodium NitrateHCID 21482728HCID 21482728, compound

Product 1

HCID 214827414-Acetylamino-3,5-bis-trifluoromethylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

5.7 G. of 4-acetylamino-3,5-bis-trifluoromethylaniline is dissolved in 16 ml. of acetic acid and cooled to 10° C., 3.2 ml. of concentrated hydrochloric acid is added, and the mixture cooled to 0°-5° C. with stirring. A solution of 1.4 g. of sodium nitrate in 4 ml. of water is added dropwise, with vigorous stirring and the resultant mixture stirred for 1/2 hour. The aqueous diazonium salt solution is then added to a solution of 0.4 g. of cupric chloride in 50 ml. of acetic acid which has been previously saturated at 20° C. with sulfur dioxide. The reaction mixture is stirred for 10 minutes, while sulfur dioxide is bubbled through this mixture and for 20 minutes further. The reaction mixture is poured into ice, extracted with methylene chloride, washed with water, dried and evaporated in vacuo. The residual 4-acetylamino-3,5-bis-trifluoromethylbenzenesulfonylchloride is again dissolved in methylene chloride and added to an excess of liquid ammonia. The contents of the flask is allowed to evaporate at room temperature overnight, affording 4 -acetylamino-3,5-bis-trifluoromethylbenzenesulfonamide. This is taken up with 25 ml. of 6N hydrochloric acid and treated on a steam bath for 3 hours. It is cooled in ice and allowed to crystallize. The residue is collected by filtration, washed with water, and crystallized from aqueous ethanol to afford pure 4-amino-3,5-trifluoromethylbenzenesulfonamide.

Workup

  1. temperaturethe mixture cooled to 0°-5° C.
  2. stirringwith vigorous stirring
  3. customis bubbled through this mixture and for 20 minutes further
  4. additionThe reaction mixture is poured into ice
  5. extractionextracted with methylene chloride
  6. washwashed with water
  7. customdried
  8. customevaporated in vacuo
  9. dissolutionThe residual 4-acetylamino-3,5-bis-trifluoromethylbenzenesulfonylchloride is again dissolved in methylene chloride
  10. additionadded to an excess of liquid ammonia
  11. customto evaporate at room temperature overnight

Sources & evidence

ORD record
ord-69558cce81df4932b01c60c7ee4c9d4d
Source dataset
uspto-grants-1976_10
Patent number
US03987199

Reaction notes

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