Water → 4'-Chloro-4-cyano-N-ethyl-2'-nitrobenzenesulfonanilide

HRID 1356704

Reaktionsgleichung

Reaktionsgleichung von HRID 1356704
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([NH:8][CH2:9][CH3:10])=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1.[C:16]([C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1)#[N:17].O>O1CCCC1>[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([N:8]([CH2:9][CH3:10])[S:24]([C:21]2[CH:20]=[CH:19][C:18]([C:16]#[N:17])=[CH:23][CH:22]=2)(=[O:26])=[O:25])=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 394974-Cyanobenzenesulfonyl chlorideHCID 97006Benzenamine, 4-chloro-N-ethyl-2-nitro-

Produkt 1

HCID 185092654'-Chloro-4-cyano-N-ethyl-2'-nitrobenzenesulfonanilideAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (60%, 0.10 g (2.50 mmol)) in tetrahydrofuran (THF)(3.0 ml), 4-chloro-N-ethyl-2-nitroaniline (0.40 g (1.99 mmol)) was added with stirring at room temperature. To the mixture, after stirring for 30 minutes at room temperature, 4-cyanobenzenesulfonyl chloride (0.50 g (2.48 mmol)) was added and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:2) as eluent, to give 0.47 g (64%) of the title compound as pale yellow crystals.

Aufarbeitung

  1. additionwas added
  2. stirringTo the mixture, after stirring for 30 minutes at room temperature
  3. stirringthe resulting mixture was stirred at room temperature for 3 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ee92ba0fa7e3409690faf65a571f39f1
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586617B1

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