Cinnamic acid, p-hydroxy-, acetate → 4-Amidino-2-benzoylphenyl 4-acetyloxycinnamate

HRID 1589504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1589504
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CS(O[C:21]1[CH:26]=[CH:25][C:24]([C:27](=[NH:29])[NH2:28])=[CH:23][C:22]=1[C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=O)=O>N1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([O:13][C:21]2[CH:26]=[CH:25][C:24]([C:27](=[NH:28])[NH2:29])=[CH:23][C:22]=2[C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 85857Cinnamic acid, p-hydroxy-, acetateHCID 540991824-Amidino-2-benzoylphenol methanesulfonate

Produkt 1

HCID 537773094-Amidino-2-benzoylphenyl 4-acetyloxycinnamateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixture of 3.1 g of 4-acetyloxycinnamic acid and 50 ml of dried pyridine, while being cooled in ice, was added 3.7 g of DDC. To the mixture, after having been stirred for 30 minutes, was added 5.0 g of 4-amidino-2-benzoylphenol methanesulfonate. The mixture was stirred overnight at room temperature. The insolubles precipitated from the reaction mixture were collected by filtration and mixed with DMF. Ethyl ether was added to the supernatant to precipitate an insoluble substance which was recrystallized from ethanol, yielding 4.7 g of colorless crystals of 4-amidino-2-benzoylphenyl 4-acetyloxycinnamate methanesulfonate.

Aufarbeitung

  1. temperaturewhile being cooled in ice
  2. additionwas added 3.7 g of DDC
  3. stirringThe mixture was stirred overnight at room temperature
  4. customThe insolubles precipitated from the reaction mixture
  5. filtrationwere collected by filtration
  6. additionmixed with DMF
  7. additionEthyl ether was added to the supernatant
  8. customto precipitate an insoluble substance which
  9. customwas recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-25d14926f5ba45c8b95ed8c3a5d8535e
Quelldatensatz
uspto-grants-1986_02
Patentnummer
US04570006

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