Acetic Acid → HCID 86722244, Verbindung

HRID 869399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869399
[NH2:1][C:2]1[C:6]2[C:7]([Cl:13])=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:14](=[O:28])[CH:15]=[CH:16][C:17]1[N:18]=[C:19]([NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[S:20][CH:21]=1.CC(O)=O.OP(O)(O)=O>CC#N.[Cl-].[Cl-].[Zn+2]>[Cl:13][C:7]1[C:6]2[C:2]3[NH:1][CH:16]([C:17]4[N:18]=[C:19]([NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[S:20][CH:21]=4)[CH2:15][C:14](=[O:28])[C:3]=3[O:4][C:5]=2[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 1004Phosphoric AcidHCID 86722243HCID 86722243, Verbindung

Produkt 1

HCID 86722244HCID 86722244, VerbindungAusbeute 19,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 11E (2.6 g, 6.19 mmol) in MeCN (30 mL) was added ZnCl2 (1.27 g, 1.5 eq, 9.3 mmol) at room temperature, followed by AcOH (30 mL) and H3PO4 (30 mL) The reaction mixture was stirred 80° C. overnight. After reaction completed, the mixture was cooled and poured into crushed ice under stirring, neutralized to pH=7˜8, extracted with ethyl acetate, dried and concentrated to give 1.6 g of crude product, which was purified by column chromatography on silica gel to give 500 mg of pure product (11F).

Aufarbeitung

  1. customAfter reaction
  2. temperaturethe mixture was cooled
  3. additionpoured
  4. custominto crushed ice
  5. stirringunder stirring
  6. extractionextracted with ethyl acetate
  7. customdried
  8. concentrationconcentrated
  9. customto give 1.6 g of crude product, which
  10. customwas purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8de8db36e93743beac580d3ea7b1ab47
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969373B2

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