Reaktion #1164441

Reaktionsgleichung

4-amino-3-hydrazino-1,2,4-triazole dihydrochloride

ethyl bromide

iodine

triethyl orthoformate

magnesium

hydrochloric acid

2,6-dimethylbromobenzene

→

4-Amino-3-(2,6-dimethylbenzylidenehydrazino)-1,2,4-triazole hydrochloride

Lösungsmittel

ethanol

ethanol

ether

water

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution was refluxed for 2 hours
2. 2
   Temperaturthe reaction mixture was refluxed for 1.5 hour
3. 3
   workup.ADDITIONTo the solution was added dropwise
4. 4
   Temperaturcooling
5. 5
   workup.WAITThe stirring was continued for 30 minutes
6. 6
   SonstigeThe ether layer was separated
7. 7
   Sonstigethe ether removed
8. 8
   Sonstigeby evaporating
9. 9
   workup.STIRRINGThe mixture was stirred
10. 10
    Temperaturheated
11. 11
    Temperaturat reflux for 5 hours
12. 12
    Temperaturthe solution cooled
13. 13
    FiltrationAfter filtration and evaporation of the solvent 3.6 g of the crude salt
14. 14
    Sonstigewas obtained
15. 15
    SonstigeAfter recrystallization from ethanol-2N hydrochloric acid

Vorschrift

In an atmosphere of dry nitrogen, a solution of 9.25 g (0.05 mole) of 2,6-dimethylbromobenzene in 100 ml of ether was added dropwise with stirring to 1.2 g (0.05 g atom) of magnesium turnings in 20 ml of ether. The reaction was started by the addition of ethyl bromide and a crystal of iodine. When all the halide had been added, the solution was refluxed for 2 hours. 8.2 ml (0.052 mole) of triethyl orthoformate was added dropwise and the reaction mixture was refluxed for 1.5 hour and left overnight at room temperature. To the solution was added dropwise while stirring and cooling a mixture of 50 ml of concentrated hydrochloric acid and 50 ml of water. The stirring was continued for 30 minutes. The ether layer was separated and the ether removed by evaporating. To the residue was added a solution of 9.35 g (0.05 mole) 4-amino-3-hydrazino-1,2,4-triazole dihydrochloride in 130 ml of 75 percent ethanol. The mixture was stirred and heated at reflux for 5 hours. 600 ml of ethanol was added and the solution cooled. After filtration and evaporation of the solvent 3.6 g of the crude salt was obtained. After recrystallization from ethanol-2N hydrochloric acid, the product melts at 219°-220° (D).

Quelle