O-Phenylenediamine → Thiabendazole

HRID 1033529

Reaktionsgleichung

Reaktionsgleichung von HRID 1033529
[C:1]([C:3]1[N:4]=[CH:5][S:6][CH:7]=1)#[N:2].Cl.Cl.[C:10]1(N)[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].[OH-].[Na+].C1(N)C=CC=CC=1N>O>[CH:14]1[CH:15]=[CH:10][C:11]2[N:16]=[C:1]([C:3]3[N:4]=[CH:5][S:6][CH:7]=3)[NH:2][C:12]=2[CH:13]=1

Komponenten

6

Edukt 4

HCID 7243O-PhenylenediamineHCID 119901,2-Phenylenediamine dihydrochlorideHCID 14798Sodium Hydroxide2×HCID 150694-Cyanothiazole2×

Produkt 1

HCID 5430ThiabendazoleAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a 1 liter four-neck flask equipped with a mechanical stirrer, a condenser, pH probe and thermometer were added 54 grams (0.5 mole) of 4-cyanothiazole, 90.5 grams (0.5 mole) of o-phenylenediamine dihydrochloride and 250 ml of deionized water. Sodium hydroxide pellets were added in sufficient proportion to increase the pH of the reaction mixture to a value of 4.0. The mixture was heated to reflux and held at reflux (100°-102° C.) for 4 hours. The reaction was determined to be complete when the peaks corresponding to o-phenylenediamine and 4-cyanothiazole were absent from the gas chromatogram. The reaction mass was allowed to cool to room temperature before adding 0.1N NaOH to adjust the pH to a value within a range of 8-10. The product was filtered, washed three times with 300 ml portions of deionized water, and then dried overnight in a vacuum oven. A total of 78.0 grams of thiabendazole were obtained which corresponds to a 77.5% yield.

Aufarbeitung

  1. customTo a 1 liter four-neck flask equipped with a mechanical stirrer, a condenser
  2. temperatureto increase the pH of the reaction mixture to a value of 4.0
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. temperatureat reflux (100°-102° C.) for 4 hours
  6. filtrationThe product was filtered
  7. washwashed three times with 300 ml portions of deionized water
  8. customdried overnight in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-bd02c7687bd94a1ea592eff0ff07e3d4
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310924

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