Ethanol → HCID 10133536, Verbindung

HRID 2307374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307374
[Cl:1][C:2]1[CH:3]=C([CH:7]=[CH:8][C:9]=1[C:10]([N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][N:15]2[CH:23]=[CH:24][CH:25]=[C:14]2[CH2:13]1)=[O:11])C#N.[OH-:26].[Na+].[CH2:28]([OH:30])[CH3:29]>>[Cl:1][C:2]1[CH:3]=[C:29]([CH:7]=[CH:8][C:9]=1[C:10]([N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][N:15]2[CH:23]=[CH:24][CH:25]=[C:14]2[CH2:13]1)=[O:11])[C:28]([OH:26])=[O:30]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 10132459HCID 10132459, Verbindung

Produkt 1

HCID 10133536HCID 10133536, Verbindung

Versuchsvorschrift

To a suspension of 3-chloro-4-(5H,11H-pyrrolo-[2,1-c][1.4]-benzodiazepine-10-carbonyl)-benzonitrile (90.72 g) in ethanol was added 10 N sodium hydroxide (1.02 ml) and the mixture heated under reflux for two hours. The solvent was removed in vacuo, the residue dissolved in water, and made acidic with 2 N hydrochloric acid (4.7 ml). The resulting precipitate was extracted with ethyl acetate, and the organic phase dried over anhydrous sodium sulfate. After removing the solvent in vacuo, a foam was triturated with diethyl ether for 18 hours and filtered to give a crude product (0.69 g). The crude product was purified by treatment with activated charcoal in methanol. Crystallization from methanol/ether afforded the title compound as a purified solid (0.29 g), m.p. 198-199° C.; MS (EI), m/z: 366 (M)+.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureunder reflux for two hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in water
  5. extractionThe resulting precipitate was extracted with ethyl acetate
  6. dry with materialthe organic phase dried over anhydrous sodium sulfate
  7. customAfter removing the solvent in vacuo
  8. customa foam was triturated with diethyl ether for 18 hours
  9. filtrationfiltered
  10. customto give a crude product (0.69 g)
  11. customThe crude product was purified by treatment with activated charcoal in methanol
  12. customCrystallization from methanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-6e8552cee4e547c0b333960321698237
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06831079B1

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