Ammonia → Nordiazepam

HRID 1973061

Reaktionsgleichung

Reaktionsgleichung von HRID 1973061
[Cl:1][C:2]1[CH:3]=[CH:4]C=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.C1N2CN3[CH2:25][N:19](C2)CN1C3.[NH3:26].[CH2:27]([OH:29])[CH3:28]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:25]2[NH:19][C:27](=[O:29])[CH2:28][N:26]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]=2[CH:15]=1

Komponenten

5

Edukt 4

HCID 222Ammonia3×HCID 702EthanolHCID 4101HexamethylenetetramineHCID 660983-Chlorobenzophenone

Produkt 1

HCID 2997Nordiazepam

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

13.5 liters of 95% ethanol, 900 gms. of 2-chloroacetamido, 5-chlorobenzophenone and 925 gms. of hexamethylenetetramine were charged to a stirred pressure vessel. The medium was saturated with ammonia gas at ch. 15# gauge of pressure with stirring. The ammonia supply was turned off. The resultant medium was heated for three hours at 78°-80° C. After cooling and venting the ammonia, the batch was removed from the pressure vessel to a vacuum still. The batch was concentrated to dryness in vacuo from a steam bath. The the residue was added 21/2 liters of toluene and 5.0 g. of p-toluenesulfonic acid and the resultant mixture was heated to reflux. Ca. 5 mls. of water formed, removed by azeotropism. After cooling to 70° C. three liters of water at 70° C. were added. The crystal slurry so obtained was cooled for one hour at +10° to +15° C. After filtering, washing the product with 2 × 250 ml. of tap water and once with 250 ml. of cold (+10° C.) toluene and drying to constant weight, 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one was obtained.

Aufarbeitung

  1. temperatureThe resultant medium was heated for three hours at 78°-80° C
  2. temperatureAfter cooling
  3. customthe batch was removed from the pressure vessel to a vacuum still
  4. concentrationThe batch was concentrated to dryness in vacuo from a steam bath
  5. additionThe the residue was added 21/2 liters of toluene and 5.0 g
  6. temperatureof p-toluenesulfonic acid and the resultant mixture was heated to reflux
  7. customof water formed
  8. customremoved by azeotropism
  9. additionwere added
  10. customThe crystal slurry so obtained
  11. temperaturewas cooled for one hour at +10° to +15° C
  12. filtrationAfter filtering
  13. washwashing the product with 2 × 250 ml
  14. dry with materialof cold (+10° C.) toluene and drying to constant weight

Quellen und Nachweise

ORD-Eintrag
ord-a8c31ec4e46846d6b4434deb95ad11d5
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03996209

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