1,2-Dichlorobenzene → N-(2-chloro-4-trifluoromethylphenyl)-2-chloro-5-trifluoromethylbenzenesulfonamide

HRID 2309005Notes

Reaction equation

HRID 2309005 reaction equation
ClC1C=CC=CC=1Cl.[Cl:9][C:10]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:11]=1[NH2:12].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=1[S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[Cl:9][C:10]1[CH:16]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:14]=[CH:13][C:11]=1[NH:12][S:32]([C:23]1[CH:24]=[C:25]([C:28]([F:29])([F:30])[F:31])[CH:26]=[CH:27][C:22]=1[Cl:21])(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 1620012-Chloro-4-trifluoromethylanilineHCID 27342742-Chloro-5-(trifluoromethyl)benzene-1-sulfonyl chloride

Product 1

HCID 13798212N-(2-chloro-4-trifluoromethylphenyl)-2-chloro-5-trifluoromethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 400 ml flask, 200 ml of o-dichlorobenzene, 1 ml of pyridine and 2.0 g (0.01 mole) of 2-chloro-4-trifluoromethylaniline were charged. While stirring the contents, 2.8 g (0.01 mole) of 2-chloro-5-trifluoromethylbenzenesulfonylchloride was added dropwise at room temperature over 5 minutes. Thereafter, the reaction mixture was heated and stirred for 8 hours under reflux (175°-180° C.). After cooling the reaction mixture to room temperature, it was thoroughly washed first with dilute hydrochloric acid and then with water. Subsequent to its dehydration with anhydrous sodium sulfate, o-dichlorobenzene was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (eluent: benzene) to isolate the intended Compound 2. m.p. 122°-123° C., yield 2.2 g (50%).

Workup

  1. additionwas added dropwise at room temperature over 5 minutes
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux (175°-180° C.)
  4. washit was thoroughly washed first with dilute hydrochloric acid
  5. distillationSubsequent to its dehydration with anhydrous sodium sulfate, o-dichlorobenzene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-748cfee77ef746e09f5d61814c14f7c1
Source dataset
uspto-grants-1987_09
Patent number
US04692466

Reaction notes

Loading…