Reaktion #55385

Reaktionsgleichung

Ethoxyacetyl chloride

4-methylthiosemicarbazide

→

3-ethoxymethyl-4-methyl-1,2,4-triazoline-5-thione

Ausbeute 65.8%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto attain room temperature
2. 2
   Einengenconcentration under reduced pressure the residue
3. 3
   workup.ADDITIONwas treated with a solution of sodium (21.4 g) in ethanol (500 ml)
4. 4
   Temperaturthe mixture was heated
5. 5
   Temperaturunder reflux for 24 hours
6. 6
   Einengenconcentration and acidification with hydrochloric acid a solid
7. 7
   Sonstigewas obtained
8. 8
   EinengenAfter partial concentration the solid
9. 9
   Sonstigewas collected
10. 10
    Sonstigerecrystallised from ethyl acetate

Vorschrift

Ethoxyacetyl chloride (57 g) was added slowly to a stirred solution of 4-methylthiosemicarbazide (53.5 g) in dry pyridine (500 ml) at 0°-5°. The mixture was allowed to attain room temperature and stirring was continued for 18 hours. Following concentration under reduced pressure the residue was treated with a solution of sodium (21.4 g) in ethanol (500 ml) and the mixture was heated under reflux for 24 hours. Following concentration and acidification with hydrochloric acid a solid was obtained. After partial concentration the solid was collected and recrystallised from ethyl acetate to give 3-ethoxymethyl-4-methyl-1,2,4-triazoline-5-thione (53 g) m.p. 137°-138°.

Quelle