Beta-Alanine → 2-Benzylidene-4-methyl-3-oxo-N-phenylpentanamide

HRID 5690

반응식

HRID 5690 반응식
[CH3:1][CH:2]([CH3:15])[C:3](=[O:14])[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].NCCC(O)=O.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(=O)C.O>[CH3:1][CH:2]([CH3:15])[C:3](=[O:14])[C:4](=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6]

참가 물질

6

반응물 3

HCID 239Beta-AlanineHCID 240BenzaldehydeHCID 102198994-methyl-3-oxo-N-phenylpentanamide

생성물 1

HCID 533948662-Benzylidene-4-methyl-3-oxo-N-phenylpentanamide수율 84.7%

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 962Water용매

실험 절차

A suspension of 100 kg of 4-methyl-3-oxo-N-phenyl-pentanamide (Example B) in 660 kg of hexanes is treated with agitation under nitrogen with 8 kg of β-alanine, 47 kg of benzaldehyde, and 13 kg of glacial acetic acid. The resulting suspension is heated to reflux with removal of water for 20 hours. An additional 396 kg of hexanes and 3 kg of glacial acetic acid is added and reflux continued with water removal for one hour. The reaction mixture is cooled to 20°-25° C. and the product is isolated by filtration. The product is purified by slurrying in hexanes at 50°-60° C., cooling, and filtration. The product is slurried twice with water at 20°-25° C., filtered, and dried in vacuo to yield 110 kg of 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide, mp 143.7°-154.4° C.

후처리

  1. temperatureThe resulting suspension is heated
  2. temperaturereflux
  3. customcontinued with water removal for one hour
  4. temperatureThe reaction mixture is cooled to 20°-25° C.
  5. customthe product is isolated by filtration
  6. customThe product is purified
  7. customby slurrying in hexanes at 50°-60° C.
  8. temperaturecooling
  9. filtrationfiltration
  10. customis slurried twice with water at 20°-25° C.
  11. filtrationfiltered
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-37e8689612b643c69b9ba6881e96180a
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245047

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