反応 #1375804

反応方程式

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

収率 131.8%

溶媒

methanol

反応条件

後処理

1. 1
   温度at reflux temperature
2. 2
   その他the 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
   ろ過was filtered off
6. 6
   洗浄washed with water
7. 7
   その他dried 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
    温度at reflux temperature
11. 11
    ろ過The charcoal was filtered off while hot and
12. 12
    洗浄washed with 2-propanol
13. 13
    その他The product was crystallized
14. 14
    ろ過filtered off
15. 15
    その他dried in vacuo at 50° C.

実験手順

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%.

出典