反応 #1435678

反応方程式

sodium sulfide nonahydrate

methyl 2,3-diaminobenzoate

N-acetylpiperidine-4-carbaldehyde

hydrochloricacid

→

product

収率 75.0%

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

収率 75.0%

溶媒

water

water

water

methanol

methanol

反応条件

後処理

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   温度the whole was refluxed for 30 minutes
3. 3
   温度After cooling
4. 4
   温度the 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
   温度After cooling
8. 8
   その他the reaction solution was evaporated down under reduced pressure
9. 9
   その他The residue obtained
10. 10
    ろ過filtered
11. 11
    抽出was extracted several times with ethyl acetate
12. 12
    洗浄The combined organic phases were washed with water
13. 13
    その他dried
14. 14
    その他evaporated down under reduced pressure

実験手順

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.

出典