Ethacrynic Acid → 2,3-Dichloro-4-[4-(dimethylaminocarbonyl)-6-ethyl-3-oxo-1-cyclohexen-1-yl]phenoxy-acetic acid

HRID 2413840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2413840
[CH3:1][N:2]([CH3:9])[C:3](=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[Na].[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24](=O)[C:25](=[CH2:28])[CH2:26][CH3:27])[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17]>C(O)C>[Cl:11][C:12]1[C:22]([Cl:23])=[C:21]([C:24]2[CH:25]([CH2:26][CH3:27])[CH2:28][CH:4]([C:3]([N:2]([CH3:9])[CH3:1])=[O:8])[C:5](=[O:6])[CH:7]=2)[CH:20]=[CH:19][C:13]=1[O:14][CH2:15][C:16]([OH:18])=[O:17]

Komponenten

5

Edukt 3

HCID 3278Ethacrynic AcidHCID 16278DimethylacetoacetamideHCID 5360545Sodium

Produkt 1

HCID 140764692,3-Dichloro-4-[4-(dimethylaminocarbonyl)-6-ethyl-3-oxo-1-cyclohexen-1-yl]phenoxy-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N,N-Dimethylacetoacetamide (13.7 g, 0.1062M) was added at 65° to a solution of sodium (2.44 g, 0.1062M) dissolved in ethanol (200 ml). After 3-5 minutes [2,3-dichloro-4-(2-methylenebutyryl)phenoxy]acetic acid (15.2 g, 0.05M) was added and the suspension was stirred at reflux for 4 hours, cooled and concentrated. The residue was taken up in water, acidified with hydrochloric acid and extracted with chloroform. The organic extracts were washed with water and concentrated. The residue was recrystallized from acetonitrile and then from a mixture of water and acetic acid to obtain 2,3-dichloro-4-[4-(dimethylaminocarbonyl)-6-ethyl-3-oxo-1-cyclohexen-1-yl]phenoxy-acetic acid, m.p. 211° (d).

Aufarbeitung

  1. temperatureat reflux for 4 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. extractionextracted with chloroform
  5. washThe organic extracts were washed with water
  6. concentrationconcentrated
  7. customThe residue was recrystallized from acetonitrile
  8. additionfrom a mixture of water and acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-6a002b8a6c3c4458b409eaab656b824b
Quelldatensatz
uspto-grants-1988_01
Patentnummer
US04719310

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