Ammonia → Nordiazepam

HRID 1973066

Reaktionsgleichung

Reaktionsgleichung von HRID 1973066
C1N2CN3CN(C2)C[N:2]1C3.Cl[CH2:12][C:13]([NH:15][C:16]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:17]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)=[O:14].N>CO>[Cl:30][C:27]1[CH:28]=[CH:29][C:16]2[NH:15][C:13](=[O:14])[CH2:12][N:2]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:17]=2[CH:26]=1

Komponenten

5

Edukt 3

HCID 222Ammonia3×HCID 4101HexamethylenetetramineHCID 776355-Chloro-2-(chloroacetamido)benzophenone

Produkt 1

HCID 2997NordiazepamAusbeute 624,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methanol (550 mls), hexamethylenetetramine (14.1 g., 0.1 mol) and 2-chloroacetamido-5-chlorobenzophenone (308.2 g., 1.0 mol) was stirred and saturated with ammonia at room temperature. The mixture was heated slowly to reflux with a steady stream of ammonia bubbling through the solution. Refluxing was continued for 24 hours. The flow of ammonia was interrupted and the crystal slurry obtained was cooled to room temperature. The product, filtered, washed with methanol (2 × 125 ml) and hot water (4 × 500 ml), and dried gave 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (169 g., 62.3%) melting at 213° to 215° C.

Aufarbeitung

  1. temperatureThe mixture was heated slowly
  2. temperatureRefluxing
  3. customthe crystal slurry obtained
  4. filtrationThe product, filtered
  5. washwashed with methanol (2 × 125 ml) and hot water (4 × 500 ml)
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-57f62855293a4e2eb21841d79ab5dc2c
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03996209

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