Isopropanol → Nordiazepam

HRID 262942

Reaktionsgleichung

Reaktionsgleichung von HRID 262942
Br[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O)=[O:4].C1N2CN3CN(C2)C[N:22]1C3.[Br-].[NH4+].C(O)(C)C>O>[Cl:20][C:17]1[CH:18]=[CH:19][C:6]2[NH:5][C:3](=[O:4])[CH2:2][N:22]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]=2[CH:16]=1

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 4101HexamethylenetetramineHCID 25514Ammonium BromideHCID 122906N-(2-benzoyl-4-chlorophenyl)-2-bromoacetamide

Produkt 1

HCID 2997Nordiazepam

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Reflux 1.76 g. (0.005 moles) of 2-(2-bromoacetamido)-5-chlorobenzophenone, 2.80 g. (0.02 moles) of hexamethylenetetramine and 1.96 g. (0.020 moles) of ammonium bromide in 14 ml. of 85% (v/v) aqueous isopropyl alcohol for 2 hours. Pour the reaction mixture into water and extract with benzene. Dry the benzene solution over anhydrous sodium sulfate. Filter and evaporate to dryness. After recrystallization, 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one is obtained. In thin layer chromatography the product shows a single spot (silica gel GF plates, benzene-ethyl acetate-acetic acid=18:3:1), m.p. 213°-215° C.

Aufarbeitung

  1. temperatureReflux 1.76 g
  2. extractionextract with benzene
  3. dry with materialDry the benzene solution over anhydrous sodium sulfate
  4. filtrationFilter
  5. customevaporate to dryness
  6. customAfter recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-ad88811aefa04662a886b06114cab536
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04155904

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