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Water → 1-(p-Chlorobenzenesulfonyloxy)-1,2,3-benzotriazole

HRID 1733708
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1733708
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.O>C1C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:1][N:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N:4]=[N:3]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 757711-Hydroxybenzotriazole

Produkt 1

HCID 203000021-(p-Chlorobenzenesulfonyloxy)-1,2,3-benzotriazoleAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241
Benzene
Lösungsmittel
2×

Versuchsvorschrift

In benzene (40 ml) are dissolved 1-hydroxy-1,2,3-benzotriazole (10.6 g) and triethylamine (11.1 ml). To the solution is added dropwise a solution of p-chlorobenzenesulfonyl chloride (16.6 g) in benzene (8 ml) with stirring under ice-cooling during about 20 minutes, and the mixture is stirred at 15° C. for 4 hours. To the reaction mixture is added water and the benzene layer is separated. The aqueous layer is extracted twice with ethyl acetate (100 ml). The extract is combined with the above benzene layer, washed with a small amount of an aqueous sodium hydrogen carbonate and water in order and dried over anhydrous sodium sulfate. After drying, the solvent is distilled off under a reduced pressure. The resulting crystals are cracked in petroleum ether and separated by filtration and dried to give faint yellow crystals of 1-(p-chlorobenzensulfonyloxy)-1,2,3-benzotriazole (21.2 g), melting point: 94°-95° C. Ultraviolet spectrum (methanol): λmax 224 mμ, E=365.

Aufarbeitung

  1. temperaturecooling during about 20 minutes
  2. stirringthe mixture is stirred at 15° C. for 4 hours
  3. customthe benzene layer is separated
  4. extractionThe aqueous layer is extracted twice with ethyl acetate (100 ml)
  5. washwashed with a small amount of an aqueous sodium hydrogen carbonate and water in order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter drying
  8. distillationthe solvent is distilled off under a reduced pressure
  9. customseparated by filtration
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-80330615c3f24330af5df6c798bb36c1
Quelldatensatz
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04242507

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