Réaction #6559

Équation de réaction

aniline

toluene

methyl 4-methyl-3-oxopentanoate

ethylenediamine

→

4-methyl-3-oxo-N-phenylpentanamide

Rendement 157.4%

Solvants

water

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONa thermometer, and set up for distillation
2. 2
   Températureto 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
   Autreis removed
9. 9
   Autrea further 550 mL of solvent is removed by vacuum distillation (using approximately 85 mm Hg)
10. 10
    TempératureThe mixture is cooled
11. 11
    workup.ADDITION2 L of water is charged
12. 12
    Autreto provide an oil
13. 13
    TempératureThe mixture is warmed to 40° C.
14. 14
    AutreSeven 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
    AutreThe product is isolated by filtration
18. 18
    Lavagewashed with three portions of hexane
19. 19
    AutreDrying in vacuo

Mode opératoire

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.

Source