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Hydrochloric Acid → HCID 86614657, Verbindung

HRID 1983849
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1983849
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:29]=[C:30](/[CH:34]=[CH:35]/[C:36]([O:38]CCCC)=[O:37])[CH:31]=[CH:32][CH:33]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH3:43].C(O)C.[OH-].[Na+].Cl>CC(C)=O>[CH3:5][C:10]([CH3:11])=[O:9].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:29]=[C:30](/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37])[CH:31]=[CH:32][CH:33]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[C:24]([F:25])([F:27])[F:26])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH3:43]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86614656HCID 86614656, Verbindung

Produkt 1

HCID 86614657HCID 86614657, VerbindungAusbeute 168,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of butyl(2E)-3-{3-[7-chloro-3-(2-{[4-fluoro-2-(trifluoromethyl)phenyl]amino}-2-oxoethyl)-6-methyl-2-oxo-2H-chromen-4-yl]phenyl}acrylate (3.0 g), ethanol (9 ml) and 2N NaOH (9 ml) was stirred at 50° C. for 1.5 hours. After completion of the reaction, acetone (27 ml) was added to the reaction mixture at 50° C., and 6N HCl (3.5 ml) was added dropwise thereto to adjust pH to 0.6. The mixture was stirred at 50° C. for 30 minutes and then at 25° C. for 1 hour, and crystals were collected by filtration, and washed with acetone/water (2/1, 6 ml). To a mixture of the resulting crystals (2.79 g), acetone (2 ml) and water (6 ml) was added dropwise 5% aqueous ammonia (2.1 ml) with stirring at room temperature to adjust pH to 9.2 and dissolve the mixture. Toluene (4.5 ml) was added to the resulting solution and the mixture was stirred for 5 minutes and allowed to stand for 5 minutes to separate an aqueous layer. Acetone (12 ml) and activated charcoal (0.15 g) were added to the obtained aqueous layer and the mixture was stirred at room temperature for 15 minutes. The activated charcoal was removed by filtration, and washed with acetone (6 ml). The filtrate and washings were combined and warmed to 50° C., and 6N HCl (1.25 ml) was added dropwise thereto with keeping the temperature almost the same and stirring to adjust pH to 0.5 and precipitate crystals. The mixture was stirred at 50° C. for 30 minutes and then at about 25° C. for 1 hour, and the crystals were collected by filtration and washed with acetone/water (2/1, 6 ml) to obtain the title compound (2.54 g, yield 84.8%). This product contained 0.9 mol of acetone.

Aufarbeitung

  1. additionwas added to the reaction mixture at 50° C.
  2. stirringThe mixture was stirred at 50° C. for 30 minutes
  3. waitat 25° C. for 1 hour
  4. filtrationcrystals were collected by filtration
  5. washwashed with acetone/water (2/1, 6 ml)
  6. additionTo a mixture of the resulting crystals (2.79 g), acetone (2 ml) and water (6 ml)
  7. additionwas added dropwise 5% aqueous ammonia (2.1 ml)
  8. stirringwith stirring at room temperature
  9. dissolutiondissolve the mixture
  10. additionToluene (4.5 ml) was added to the resulting solution
  11. stirringthe mixture was stirred for 5 minutes
  12. waitto stand for 5 minutes
  13. customto separate an aqueous layer
  14. additionAcetone (12 ml) and activated charcoal (0.15 g) were added to the obtained aqueous layer
  15. stirringthe mixture was stirred at room temperature for 15 minutes
  16. customThe activated charcoal was removed by filtration
  17. washwashed with acetone (6 ml)
  18. temperaturewarmed to 50° C.
  19. addition6N HCl (1.25 ml) was added dropwise
  20. stirringstirring
  21. stirringThe mixture was stirred at 50° C. for 30 minutes
  22. waitat about 25° C. for 1 hour
  23. filtrationthe crystals were collected by filtration
  24. washwashed with acetone/water (2/1, 6 ml)

Quellen und Nachweise

ORD-Eintrag
ord-12b7983c10db4dceb33956777326f5b5
Quelldatensatz
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07541478B2

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