Reaktion #54928

Reaktionsgleichung

ethanol

1-methyl-1-(o-toluyl)-hydrazine

m-chlorobenzimidic acid ethyl ester

hydrochloride

m-chlorobenzimidic acid ethyl ester

sodium

→

crude product

Ausbeute 66.0%

1-Methyl-3-(3-chlorophenyl)-5-(o-tolyl)-1,2,4-triazole

Ausbeute 66.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 6.85 g
2. 2
   workup.DISTILLATIONsimultaneously ethanol and m-chlorobenzonitrile are distilled off
3. 3
   workup.ADDITIONof ethanol are added
4. 4
   Sonstigeprepared from 0.336 g
5. 5
   TemperaturThe mixture is refluxed for 6 hours
6. 6
   workup.WAITafter standing over night
7. 7
   Filtrationthe insoluble precipitate is filtered off
8. 8
   SonstigeThe filtrate is evaporated to dryness
9. 9
   workup.DISSOLUTIONThe residue is dissolved in 100 ml
10. 10
    Waschenof diethyl ether and after washing the organic layer successively with aqueous 5% Na2CO3, 5% HCl and water
11. 11
    Trocknenthe solution is dried over sodium sulfate

Vorschrift

A mixture of 6.85 g. of 1-methyl-1-(o-toluyl)-hydrazine, 13.8 g. of m-chlorobenzimidic acid ethyl ester and 1.8 g. of the hydrochloride of m-chlorobenzimidic acid ethyl ester is heated with stirring under vacuum for 18 hours and simultaneously ethanol and m-chlorobenzonitrile are distilled off. Then, maintaining the temperature at about 65° C., 40 ml. of ethanol are added followed by a sodium ethylate solution prepared from 0.336 g. of sodium and 20 ml. of ethanol. The mixture is refluxed for 6 hours and after standing over night, the insoluble precipitate is filtered off. The filtrate is evaporated to dryness. The residue is dissolved in 100 ml. of diethyl ether and after washing the organic layer successively with aqueous 5% Na2CO3, 5% HCl and water, the solution is dried over sodium sulfate. The crude product obtained by evaporation of the diethyl ether solution is crystallized from ethanol. Yield 66%. M.p. 77°-78° C.

Quelle