Toluene → 4-methyl-3-oxo-N-phenylpentanamide

HRID 6463

반응식

HRID 6463 반응식
C1(C)C=CC=CC=1.[CH3:8][CH:9]([CH3:17])[C:10](=[O:16])[CH2:11][C:12]([O:14]C)=O.C(N)CN.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH3:17][CH:9]([CH3:8])[C:10](=[O:16])[CH2:11][C:12]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 3301EthylenediamineHCID 6115AnilineHCID 2759969Methyl 4-methyl-3-oxopentanoate

생성물 1

HCID 102198994-methyl-3-oxo-N-phenylpentanamide수율 157.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  1. distillationa thermometer, and set up for distillation
  2. temperatureto reflux
  3. distillationdistillation
  4. 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. additionare charged
  6. distillationDistillation
  7. waitis continued for a further one to five hours until a total of 985 mL of solvent
  8. customis removed
  9. customa further 550 mL of solvent is removed by vacuum distillation (using approximately 85 mm Hg)
  10. temperatureThe mixture is cooled
  11. addition2 L of water is charged
  12. customto provide an oil
  13. temperatureThe mixture is warmed to 40° C.
  14. customSeven hundred milliliters of toluene-water mixture is removed by vacuum distillation (approximately 20 mm Hg)
  15. additionTwo liters of water is charged
  16. waitto stand for 10 days
  17. customThe product is isolated by filtration
  18. washwashed with three portions of hexane
  19. customDrying in vacuo

출처 및 근거

ORD 기록
ord-da4df0e2a9804ff7a23ad117f2bc5cf7
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248793

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