Methyl iodide → 7-Chloro-5-(2'-chloro-phenyl)-1,3-dihydro-3-(dimethylaminomethylene)-1-methyl-2H-1,4-benzodiazepin-2-one

HRID 1076391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1076391
[CH3:1][O-].[Na+].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:14][C:13](=[O:15])[C:12](=[CH:16][N:17]([CH3:19])[CH3:18])[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:9]=2[CH:27]=1.CI>CN(C)C=O>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]2[N:14]([CH3:1])[C:13](=[O:15])[C:12](=[CH:16][N:17]([CH3:19])[CH3:18])[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:9]=2[CH:27]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 1363535337-Chloro-5-(2'-chloro-phenyl)-1,3-dihydro-3-(dimethylaminomethylene)-2H-1,4-benzodiazepin-2-one

Produkt 1

HCID 536319327-Chloro-5-(2'-chloro-phenyl)-1,3-dihydro-3-(dimethylaminomethylene)-1-methyl-2H-1,4-benzodiazepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

35.6 gm of a methanolic 30% sodium methylate solution were added dropwise to a solution of 46.5 gm of 7-chloro-5-(2'-chloro-phenyl)-1,3-dihydro-3-(dimethylamino-methylene)-2H-1,4-benzodiazepin-2-one in 300 ml of dry dimethylformamide at room temperature, accompanied by stirring, and the resulting mixture was stirred for 30 minutes more at room temperature and subsequently cooled to +5°C while stirring. Then, while maintaining that temperature by cooling, 58 gm of methyl iodide were added at a slow dropwise rate, again while stirring, and the resulting mixture was stirred for 90 minutes more at +5°C. Thereafter, the yellow precipitate which had formed was collected by vacuum filtration, washed with much water, dried and recrystallized from isopropanol, yielding the compound named in the heading above, which had a melting point of 199°-200°C.

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 30 minutes more at room temperature
  2. temperaturesubsequently cooled to +5°C
  3. stirringwhile stirring
  4. temperatureThen, while maintaining that temperature
  5. temperatureby cooling
  6. stirringagain while stirring
  7. stirringthe resulting mixture was stirred for 90 minutes more at +5°C
  8. customThereafter, the yellow precipitate which had formed
  9. filtrationwas collected by vacuum filtration
  10. washwashed with much water
  11. customdried
  12. customrecrystallized from isopropanol
  13. customyielding the compound

Quellen und Nachweise

ORD-Eintrag
ord-3fff06df30a54eceb6ab33e163d6bd04
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03956492

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