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Hydrazine hydrate (1:1) → 1-benzenesulfonyl-5-methylthio-2-([1,3,4]oxadiazol-2-yl)-1H-indole

HRID 1838319
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1838319
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([S:14][CH3:15])=[CH:9][CH:8]=2)=O.P(Cl)(Cl)(Cl)=O.O.[NH2:31][NH2:32]>C(O)C>[C:19]1([S:16]([N:6]2[C:7]3[C:12](=[CH:11][C:10]([S:14][CH3:15])=[CH:9][CH:8]=3)[CH:13]=[C:5]2[C:3]2[O:2][CH:1]=[N:31][N:32]=2)(=[O:18])=[O:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24654Hydrazine hydrate (1:1)2×HCID 24813Phosphorus oxychlorideHCID 684436811-benzenesulfonyl-5-methylthio-1H-indole-2-carboxylic acid methyl ester

Produkt 1

HCID 225044011-benzenesulfonyl-5-methylthio-2-([1,3,4]oxadiazol-2-yl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-benzenesulfonyl-5-methylthio-1H-indole-2-carboxylic acid methyl ester (370 mg) in ethanol (12 ml), hydrazine monohydrate (0.55 ml) was added at 15 to 30° C. and the mixture was heated under reflux for 13 hours. Further, to the mixture was added hydrazine monohydrate (0.55 ml) and the mixture was heated under reflux for 5 hours. The reaction solution was concentrated under reduced pressure. To the resulting residue was added water, and the insolubles were filtered off and washed with water and ether. To the filtered crude product was added formic acid (9 ml) and the mixture was heated under reflux for 1 hour. The reaction solution was concentrated under reduced pressure. To the resulting residue was added ethyl acetate and the insolubles were filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to obtain 330 mg of the crude product of 1-benzenesulfonyl-5-methylthio-1H-indole-2-carboxylic acid-N′-formylhydrazide. A mixture solution of 509 mg of the crude product thus obtained and phosphorus oxychloride (15 ml) was stirred at 15 to 30° C. for 6 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 265 mg of the desired product.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 13 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 5 hours
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. additionTo the resulting residue was added water
  7. filtrationthe insolubles were filtered off
  8. washwashed with water and ether
  9. filtrationTo the filtered crude product
  10. additionwas added formic acid (9 ml)
  11. temperaturethe mixture was heated
  12. temperatureunder reflux for 1 hour
  13. concentrationThe reaction solution was concentrated under reduced pressure
  14. additionTo the resulting residue was added ethyl acetate
  15. filtrationthe insolubles were filtered off
  16. washwashed with ethyl acetate
  17. concentrationThe filtrate was concentrated under reduced pressure
  18. customto obtain 330 mg of the crude product of 1-benzenesulfonyl-5-methylthio-1H-indole-2-carboxylic acid-N′-formylhydrazide
  19. customA mixture solution of 509 mg of the crude product thus obtained
  20. concentrationThe reaction solution was concentrated under reduced pressure
  21. customThe resulting residue was separated

Quellen und Nachweise

ORD-Eintrag
ord-e7e1021b947e4393b493292f0dc666fb
Quelldatensatz
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06673797B1

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