Реакция #1375804

Уравнение реакции

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

Выход 131.8%

Растворители

methanol

Условия реакции

Обработка

1. 1
   Температураat reflux temperature
2. 2
   Другоеthe 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
   Фильтрацияwas filtered off
6. 6
   Промывкаwashed with water
7. 7
   Другоеdried 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
    Температураat reflux temperature
11. 11
    ФильтрацияThe charcoal was filtered off while hot and
12. 12
    Промывкаwashed with 2-propanol
13. 13
    ДругоеThe product was crystallized
14. 14
    Фильтрацияfiltered off
15. 15
    Другоеdried in vacuo at 50° C.

Методика

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%.

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