Reacción #1375804

Ecuación de reacción

intermediate 4-a

(+)-6-[(4-chlorophenyl)hydrazinomethyl]-1-methyl-1H-benzotriazole monohydrochloride

methanimidamide monoacetate

→

(+)-6-[(4-chloro-phenyl)-(1H-1,2,4-triazol-1 -yl) methyl]-1-methyl-1H-benzotriazole

Rendimiento 131.8%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux temperature
2. 2
   Otrothe reaction mixture crystallized
3. 3
   workup.ADDITIONthere were added 30 ml of water
4. 4
   workup.STIRRINGAfter stirring for 1 hour the precipitate
5. 5
   Filtraciónwas filtered off
6. 6
   Lavadowashed with water
7. 7
   Otrodried in vacuo at 50° C
8. 8
   workup.ADDITIONThe product was diluted with 11.8 ml of 2-propanol
9. 9
   workup.ADDITIONthe whole was treated with active charcoal for 15 min.
10. 10
    Temperaturaat reflux temperature
11. 11
    FiltraciónThe charcoal was filtered off while hot and
12. 12
    Lavadowashed with 2-propanol
13. 13
    OtroThe product was crystallized
14. 14
    Filtraciónfiltered off
15. 15
    Otrodried in vacuo at 50° C.

Procedimiento

A mixture of 5 g of intermediate 4-a, 4.8 g of methanimidamide monoacetate and 15 ml of methanol was stirred for 1.5 hours at reflux temperature. After cooling to room temperature, the reaction mixture crystallized and there were added 30 ml of water. After stirring for 1 hour the precipitate was filtered off, washed with water and dried in vacuo at 50° C. The product was diluted with 11.8 ml of 2-propanol and the whole was treated with active charcoal for 15 min. at reflux temperature. The charcoal was filtered off while hot and washed with 2-propanol. The product was crystallized, filtered off and dried in vacuo at 50° C., yielding 3.3 g (66.0%) of (+)-6-[(4-chloro-phenyl)-(1H-1,2,4-triazol-1 -yl) methyl]-1-methyl-1H-benzotriazole (comp. 1-a); mp. 130°-135° C.; [α]D20 =+8.0° (conc.=10% in CH3OH); enantiomeric excess: 98.4%.

Fuente