Benzenesulfonyl chloride → N-(2-methoxyphenyl)-2-(4-nitrophenylthio)-6-(phenylsulfonamido)benzamide

HRID 1476708

Reaktionsgleichung

Reaktionsgleichung von HRID 1476708
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:5].[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>N1C=CC=CC=1>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[NH:6][C:4](=[O:5])[C:3]1[C:2]([NH:1][S:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:37])=[O:36])=[CH:18][CH:17]=[CH:16][C:15]=1[S:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1

Komponenten

4

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 718115872-amino-N-(2-methoxyphenyl)-6-(4-nitrophenyl-thio)benzamide

Produkt 1

HCID 118402644N-(2-methoxyphenyl)-2-(4-nitrophenylthio)-6-(phenylsulfonamido)benzamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Compound 25 (1.0 equiv.) was dissolved in azabenzene (40 mL) at room temperature. To this mixture was added benzenesulfonyl chloride (1.2 equiv.). After being stirred for 10 Hours at room temperature, the reaction mixture was concentrated under reduced pressure. The crude residue was diluted ethyl acetate (50 mL), washed with water (3×20 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether) to provide a white solid. 67% yield;

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. washwashed with water (3×20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether)
  7. customto provide a white solid

Quellen und Nachweise

ORD-Eintrag
ord-6f8ebbac375646b1b282f1ad582046b0
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09402819B2

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