Nordiazepam → Diazepam

HRID 262943

Reaktionsgleichung

Reaktionsgleichung von HRID 262943
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.Cl[CH2:21]Cl.[OH-].[Na+].S(OC)(OC)(=O)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:21])[C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

Komponenten

6

Edukt 4

HCID 2997NordiazepamHCID 6344DichloromethaneHCID 6497Dimethyl Sulfate2×HCID 14798Sodium Hydroxide

Produkt 1

HCID 3016Diazepam

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolve 5.4 g. (0.02 moles) of 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (e.g. product of Example 3) in 35 ml. of dichloromethane and add to this solution 1.2 g. of NaOH (1.5 moles) dissolved in 17 ml. of water. Cool the mixture with good agitation to 0° C. and add slowly 3.8 g. (0.03 moles) of dimethyl sulfate with good cooling and stirring. After all the dimethyl sulfate is added remove the cooling bath and continue stirring for an additional 2 hours. Add water and methylene chloride to the reaction mixture. Separate the layers and wash the methylene chloride layers with water. Dry the organic solution over anhydrous sodium sulfate and evaporate. After recrystallization, 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one is obtained which after drying under vacuum at 110° C. shows a melting point of 129.5°-130.5° (corr.) and no depression on mixed melt with an authentic sample.

Aufarbeitung

  1. dissolutionDissolve 5.4 g
  2. additionadd slowly 3.8 g
  3. customremove the cooling bath
  4. stirringcontinue stirring for an additional 2 hours
  5. customSeparate the layers
  6. washwash the methylene chloride layers with water
  7. dry with materialDry the organic solution over anhydrous sodium sulfate
  8. customevaporate
  9. customAfter recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-7d297480434146ad9f723c4e39808ed7
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04155904

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