반응 #1375806

반응 방정식

intermediate 1-b

1,1-dimethylethyl [(4-chlorophenyl)(1 -methyl-1H-benzotriazol-6-yl)-methylene]hydrazine carboxylate

hydrochloric acid

water

→

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

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The whole was heated
2. 2
   온도to reflux
3. 3
   온도refluxed for 1.5 hours
4. 4
   온도The mixture was cooled to room temperature
5. 5
   workup.STIRRINGAfter stirring for 1 hour
6. 6
   여과the reaction mixture was filtered
7. 7
   workup.ADDITIONThe filtrate was mixed with 75 ml of methylbenzene
8. 8
   기타The layers were separated
9. 9
   추출The product was extracted with dichloromethane
10. 10
    기타the extract was dried
11. 11
    여과filtered
12. 12
    기타evaporated
13. 13
    workup.ADDITIONby adding 3ml of a mixture of hydrochloric acid in 2-propanol (4.8N)
14. 14
    workup.STIRRINGAfter stirring for 2 hours the product
15. 15
    여과was filtered off
16. 16
    세척washed with 2-propanol
17. 17
    기타dried in vacuo at 50° C.

실험 절차

To a suspension of 10 g of intermediate 1-b in 60 ml of tetrahydrofuran under a nitrogen atmosphere were added dropwise over 15 minutes 26 ml of a borane tetrahydrofuran complex in tetrahydrofuran (1M). After stirring for 15 minutes at ±22° C. there were added 13 ml of hydrochloric acid (6N). The whole was heated to reflux and refluxed for 1.5 hours. The mixture was cooled to room temperature and 50 ml of water were added. After stirring for 1 hour, the reaction mixture was filtered. The filtrate was mixed with 75 ml of methylbenzene. The layers were separated and the aqueous layer was basified (pH 7.5-8) with NH4OH. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was converted into the hydrochloride salt in 2-propanol by adding 3ml of a mixture of hydrochloric acid in 2-propanol (4.8N). After stirring for 2 hours the product was filtered off, washed with 2-propanol and dried in vacuo at 50° C., yielding 2.1 g of (±)-6-[(4-chlorophenyl)hydrazinomethyl]-1-methyl-1H-benzotriazole monohydrochloride (interm. 2-e).

출처