Ammonium Hydroxide → HCID 9969119, Verbindung

HRID 2307375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307375
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]#[N:6].[OH-:26].[NH4+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([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:5]([NH2:6])=[O:26]

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 10132459HCID 10132459, Verbindung

Produkt 1

HCID 9969119HCID 9969119, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Concentrated sulfuric acid (70 ml) was added to 3-chloro-4-(5H,11H-pyrrolo-[2,1-c][1.4]benzodiazepine-10-carbonyl)-benzonitrile (12.85 g). The mixture was stirred at 60° C. for 3 hours, followed by stirring at room temperature for 18 hours. The reaction mixture was poured over ice and neutralized at 0° C., with 30% ammonium hydroxide (184 ml). The resulting suspension was extracted with ethyl acetate. The aqueous mixture was filtered, and reextracted with ethyl acetate. The combined organic phase was dried over anhydrous sodium sulfate, and the solvent removed in vacuo. The residue was triturated with a mixture of diethyl ether (50-60 ml) and a small quantity of ethyl acetate. Filtration of the precipitate afforded the title compound as a crystalline solid (10.44 g), m.p. 211-212° C.; MS (EI), m/z: 365 (M)+.

Aufarbeitung

  1. stirringby stirring at room temperature for 18 hours
  2. extractionThe resulting suspension was extracted with ethyl acetate
  3. filtrationThe aqueous mixture was filtered
  4. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  5. customthe solvent removed in vacuo
  6. customThe residue was triturated with a mixture of diethyl ether (50-60 ml)
  7. filtrationFiltration of the precipitate

Quellen und Nachweise

ORD-Eintrag
ord-571eed49bcab401caa1d0cabc4ad5ccd
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06831079B1

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