Water → N-(4-Chloro-2-nitrophenyl)benzenesulfonamide

HRID 1006534

반응식

HRID 1006534 반응식
[N+:1]([C:4]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].N1C=CC=CC=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(Cl)Cl>[C:18]1([S:24]([NH:6][C:5]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 69794-Chloro-2-nitroanilineHCID 7369Benzenesulfonyl chloride

생성물 1

HCID 555628N-(4-Chloro-2-nitrophenyl)benzenesulfonamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-nitro-4-chloroaniline (500 mg) and pyridine (2.1 ml in methylene chloride (10 ml), benzenesulfonylchloride (1.2 ml) was added dropwise at 0° C. under an atmosphere of argon. The reaction mixture was stirred for 3 days at room temperature. To the reaction mixture, water was added. The mixture was extracted with ethyl acetate. The organic layer was washed, dried over and concentrated under the reduced pressure. The reside was recrystallized from AcOEt-hexane mixture solvent to give the by-product. The mother liquor was concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (AcOEt-hexane) and recrystallized from AcOEt-hexane mixture solvent to give the title compound (175 mg) having the following physical data.

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried over and
  4. concentrationconcentrated under the reduced pressure
  5. customThe reside was recrystallized from AcOEt-hexane mixture solvent
  6. customto give the by-product
  7. concentrationThe mother liquor was concentrated under the reduced pressure
  8. customThe residue was purified on silica gel column chromatography (AcOEt-hexane)
  9. customrecrystallized from AcOEt-hexane mixture solvent

출처 및 근거

ORD 기록
ord-e3f93863aaa74b9495d725b4527668a8
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790866B2

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