반응 #1435678

반응 방정식

sodium sulfide nonahydrate

methyl 2,3-diaminobenzoate

N-acetylpiperidine-4-carbaldehyde

hydrochloricacid

→

product

수율 75.0%

Methyl 2-(N-acetylpiperidin-4-yl)benzimidazole-4-carboxylate

수율 75.0%

용매

water

water

water

methanol

methanol

반응 조건

후처리

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   온도the whole was refluxed for 30 minutes
3. 3
   온도After cooling
4. 4
   온도the whole was again refluxed
5. 5
   workup.ADDITIONwere then added dropwise
6. 6
   workup.WAITthe whole was boiled for a further 10 minutes
7. 7
   온도After cooling
8. 8
   기타the reaction solution was evaporated down under reduced pressure
9. 9
   기타The residue obtained
10. 10
    여과filtered
11. 11
    추출was extracted several times with ethyl acetate
12. 12
    세척The combined organic phases were washed with water
13. 13
    기타dried
14. 14
    기타evaporated down under reduced pressure

실험 절차

3.3 g (19.9 mmol) of methyl 2,3-diaminobenzoate were dissolved in 100 ml of methanol, and a solution of 4.0 g (25.8 mmol) of N-acetylpiperidine-4-carbaldehyde in 100 ml of methanol was added dropwise at room temperature. The whole was stirred for about 10 minutes at room temperature. Thereafter, 5.2 g (25.8 mmol) of copper(II) acetate, which was dissolved in 100 ml of water, were added dropwise and the whole was refluxed for 30 minutes. After cooling, 25 ml of concentrated hydrochloricacid were added carefully and the whole was again refluxed. 7.15 g (29.8 mmol) of sodium sulfide nonahydrate, dissolved in 100 ml of water, were then added dropwise and the whole was boiled for a further 10 minutes. After cooling, the reaction solution was evaporated down under reduced pressure. The residue obtained was dispersed in water and filtered. The filtrate was rendered alkaline with aqueous sodium bicarbonate solution and was extracted several times with ethyl acetate. The combined organic phases were washed with water, dried and evaporated down under reduced pressure. 4.5 g of the product were obtained.

출처