4-(Trifluoromethyl)aniline → HCID 14480012, compound

HRID 231134Notes

Reaction equation

HRID 231134 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12]1([CH3:24])[CH:17]=[CH:16][C:15]([S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(Cl)Cl>[CH3:24][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:22]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][CH:3]=2)=[O:23])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 77703p-Toluenesulfonyl isocyanate

Product 1

HCID 14480012HCID 14480012, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 8.0 g of 4-aminobenzotrifluoride in 10 ml of methylene chloride was added to a solution of 9.85 g of p-toluenesulfonyl isocyanate in 75 ml of methylene chloride with stirring. The mixture became quite warm and a heavy white precipitate formed. An additional 100 ml of methylene chloride was added. The reaction mixture was stirred an additional 15 minutes, and the precipitate was recovered by filtration affording 15.0 g of the title product as a white solid. A small amount of the material was crystallized from diethyl ether to provide 4-methyl-N-([(4-trifluoromethylphenyl)amino]carbonyl)benzenesulfonamide with a melting point of 194°-197° C.

Workup

  1. temperatureThe mixture became quite warm
  2. customa heavy white precipitate formed
  3. stirringThe reaction mixture was stirred an additional 15 minutes
  4. filtrationthe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-7a1fd723e8334155ae09b8dd461a7738
Source dataset
uspto-grants-1989_07
Patent number
US04845128

Reaction notes

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