1,2-Dichlorobenzene → N-(2-chloro-4-nitrophenyl)-3-trifluoromethylbenzenesulfonamide

HRID 232159

反応式

HRID 232159 の反応式
ClC1C=CC=CC=1Cl.[Cl:9][C:10]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=1[NH2:12].[F:20][C:21]([F:33])([F:32])[C:22]1[CH:23]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1>N1C=CC=CC=1>[Cl:9][C:10]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=1[NH:12][S:28]([C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:20])([F:32])[F:33])[CH:23]=1)(=[O:30])=[O:29]

参加物

5

反応物 3

HCID 72391,2-DichlorobenzeneHCID 84922-Chloro-4-nitroanilineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chloride

生成物 1

HCID 13799089N-(2-chloro-4-nitrophenyl)-3-trifluoromethylbenzenesulfonamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

In a 400 ml flask, 200 ml of o-dichlorobenzene, 1 ml of pyridine and 1.7 g (0.01 mole) of 2-chloro-4-nitroaniline were charged. While stirring the contents at room temperature, 2.5 g (0.01 mole) of 3-trifluoromethylbenzenesulfonylchloride was added gradually over 30 minutes. Thereafter, the reaction mixture was heated and stirred for 8 hours under reflux (175°-180° C.) to complete the reaction. 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 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 1. m.p. 126°-127° C., yield 1.9 g (50%).

後処理

  1. temperatureThereafter, the reaction mixture was heated
  2. stirringstirred for 8 hours
  3. temperatureunder reflux (175°-180° C.)
  4. customthe reaction
  5. temperatureAfter cooling the reaction mixture to room temperature
  6. washit was thoroughly washed first with dilute hydrochloric acid
  7. distillationSubsequent to its dehydration with sodium sulfate, o-dichlorobenzene was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-16d81bc93b0d4caa95a444a199096040
出典データセット
uspto-grants-1989_07
特許番号
US04851445

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