反応 #6559

反応方程式

aniline

toluene

methyl 4-methyl-3-oxopentanoate

ethylenediamine

→

4-methyl-3-oxo-N-phenylpentanamide

収率 157.4%

溶媒

water

反応条件

後処理

1. 1
   workup.DISTILLATIONa thermometer, and set up for distillation
2. 2
   温度to reflux
3. 3
   workup.DISTILLATIONdistillation
4. 4
   workup.ADDITIONAfter 40 minutes a further 0.245 kg of aniline is charged and at 40-minute intervals a further two portions of aniline (0.245 and 0.25 kg)
5. 5
   workup.ADDITIONare charged
6. 6
   workup.DISTILLATIONDistillation
7. 7
   workup.WAITis continued for a further one to five hours until a total of 985 mL of solvent
8. 8
   その他is removed
9. 9
   その他a further 550 mL of solvent is removed by vacuum distillation (using approximately 85 mm Hg)
10. 10
    温度The mixture is cooled
11. 11
    workup.ADDITION2 L of water is charged
12. 12
    その他to provide an oil
13. 13
    温度The mixture is warmed to 40° C.
14. 14
    その他Seven hundred milliliters of toluene-water mixture is removed by vacuum distillation (approximately 20 mm Hg)
15. 15
    workup.ADDITIONTwo liters of water is charged
16. 16
    workup.WAITto stand for 10 days
17. 17
    その他The product is isolated by filtration
18. 18
    洗浄washed with three portions of hexane
19. 19
    その他Drying in vacuo

実験手順

A three-necked, 12-L round-bottom flask equipped with a mechanical stirrer, a thermometer, and set up for distillation is charged with 2.6 L of toluene, 1.73 kg (12 mol) of methyl 4-methyl-3-oxopentanoate and 72 g (1.18 mol) of ethylenediamine. The mixture is heated to 80° C. and charged with 0.49 kg of aniline. The mixture is brought to reflux and distillation started. After 40 minutes a further 0.245 kg of aniline is charged and at 40-minute intervals a further two portions of aniline (0.245 and 0.25 kg) are charged. Distillation is continued for a further one to five hours until a total of 985 mL of solvent is removed. The solution is stirred at room temperature for 16 hours and a further 550 mL of solvent is removed by vacuum distillation (using approximately 85 mm Hg). The mixture is cooled and 2 L of water is charged to provide an oil. The mixture is warmed to 40° C. and a further 1.0 L of water is charged. Seven hundred milliliters of toluene-water mixture is removed by vacuum distillation (approximately 20 mm Hg). Two liters of water is charged and the mixture is allowed to stand for 10 days. The product is isolated by filtration and washed with three portions of hexane. Drying in vacuo gives 1.7 kg of 4-methyl-3-oxo-N-phenylpentanamide as a hydrate; m.p. 46.5°-58.8° C.

出典