Acetic Acid → 1-(4-Carboxyphenyl)-4-(4-dimethylaminocinnamylidene)-3-methyl-2-pyrazolin-5-one

HRID 1381485노트

반응식

HRID 1381485 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH2:13][C:12]([CH3:16])=[N:11]2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH3:17][N:18]([CH3:29])[C:19]1[CH:28]=[CH:27][C:22]([CH:23]=[CH:24][CH:25]=O)=[CH:21][CH:20]=1.C(O)(=O)C>CCO>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[C:13](=[CH:25][CH:24]=[CH:23][C:22]3[CH:21]=[CH:20][C:19]([N:18]([CH3:29])[CH3:17])=[CH:28][CH:27]=3)[C:12]([CH3:16])=[N:11]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 922244-(Dimethylamino)-cinnamaldehydeHCID 1090294-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

생성물 1

HCID 589660201-(4-Carboxyphenyl)-4-(4-dimethylaminocinnamylidene)-3-methyl-2-pyrazolin-5-one

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

1-(4-Carboxyphenyl)-3-methyl-2-pyrazolin-5-one (2.18 gm, 0.010 mol), 4-dimethylaminocinnamaldehyde (1.75 gm, 0.010 mol) and glacial acetic acid (10 ml) were mixed together to form a slurry. It was heated to reflux with stirring, held at reflux for five minutes and then cooled to RT. EtOH (20 ml) was added to the reaction mixture which was heated again to reflux, held there for five minutes and cooled to RT. The product was isolated by filtration, washed in succession with ethanol and ligroin, and dried. The reaction was repeated twice on the same scale and the products obtained were all combined. They were treated further by first slurrying in refluxing EtOH (150 ml), isolating the solid by filtration while hot, and then slurrying in refluxing MeOH (200 ml) and isolating it again, while hot, by filtration. The mp was 282°-284° C. The NMR and IR spectra were consistent for the structure assigned. The C,H and N elemental analyses were in agreement with those calculated for the empirical formula of the dye.

후처리

  1. customto form a slurry
  2. temperatureIt was heated
  3. temperatureto reflux
  4. temperatureat reflux for five minutes
  5. temperaturewas heated again
  6. temperatureto reflux
  7. temperaturecooled to RT
  8. customThe product was isolated by filtration
  9. washwashed in succession with ethanol and ligroin
  10. customdried
  11. customthe products obtained
  12. additionThey were treated further by first slurrying
  13. customisolating the solid
  14. filtrationby filtration while hot, and
  15. temperaturein refluxing MeOH (200 ml)
  16. customisolating it again
  17. filtrationwhile hot, by filtration

출처 및 근거

ORD 기록
ord-69556223cd1c43858023013bb5608291
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04803150

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