Ammonium Hydroxide → 5-(3-Methylpentan-3-yl)-1,3,4-thiadiazol-2-amine

HRID 980102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 980102
[CH2:1]([C:3]([CH3:9])([CH2:7][CH3:8])[C:4](O)=O)[CH3:2].[NH2:10][NH:11][C:12]([NH2:14])=[S:13].P(Cl)(Cl)(Cl)=O.[OH-].[NH4+]>O1CCOCC1>[NH2:14][C:12]1[S:13][C:4]([C:3]([CH2:7][CH3:8])([CH3:9])[CH2:1][CH3:2])=[N:10][N:11]=1

Komponenten

6

Edukt 4

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 298462-Ethyl-2-methylbutyric acidHCID 2723789Thiosemicarbazide

Produkt 1

HCID 132342635-(3-Methylpentan-3-yl)-1,3,4-thiadiazol-2-amineAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution containing 13.0 g of 2-ethyl-2-methylbutyric acid and 9.1 g of thiosemicarbazide in 125 ml of dioxane was stirred and heated to 90° C. To the stirred reaction mixture was added dropwise over thirty minutes 15.3 g of phosphorus oxychloride. Following complete addition, the reaction mixture was heated at 90° C. for six hours. The mixture was then cooled to about 30° C. and added to 100 g of ice. The aqueous mixture was made alkaline by the addition of ammonium hydroxide, and the alkaline solution was extracted several times with ethyl acetate. The extracts were combined, washed with water, dried, and the solvent was removed by evaporation under reduced pressure to afford 17.0 g of 2-amino-5-(1-ethyl-1-methylpropyl)-1,3,4-thiadiazole.

Aufarbeitung

  1. customTo the stirred reaction mixture
  2. additionaddition
  3. temperaturethe reaction mixture was heated at 90° C. for six hours
  4. temperatureThe mixture was then cooled to about 30° C.
  5. extractionthe alkaline solution was extracted several times with ethyl acetate
  6. washwashed with water
  7. customdried
  8. customthe solvent was removed by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-497bff36f61f4d2ba87e5065a737b80f
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04636243

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