Hydrazine hydrate (1:1) → Estazolam

HRID 1764511

Reaktionsgleichung

Reaktionsgleichung von HRID 1764511
[NH2:1][C:2]1[CH2:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:4]=2[N:3]=1.Cl.C[C:22]1[NH:23]C=CN=1.O.NN.C([O-])([O-])OCC>C(O)C.CO>[Cl:19][C:16]1[CH:17]=[CH:18][C:4]2[N:3]3[CH:22]=[N:23][N:1]=[C:2]3[CH2:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[CH:15]=1

Komponenten

7

Edukt 4

HCID 24654Hydrazine hydrate (1:1)HCID 165626N-Desmethyl-N(4)-desoxychlordiazepoxideHCID 5216292-Methylimidazole hydrochlorideHCID 53630039Ethylorthoformate

Produkt 1

HCID 3261Estazolam

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of 8.1 parts of 2-amino-7-chloro-5-phenyl-3H-1,4-benzodiazepine in 180 parts by volume of methanol are added 3.6 parts of 2-methylimidazole hydrochloride and 2.25 parts by volume of 80% hydrazine hydrate. The suspension is stirred at room temperature for 1.5 hours, and then 25 parts of ethyl orthoformate is added. To the mixture is added dropwise with stirring 60 parts by volume of ethanol containing 10% hydrogen chloride. After stirring for a further 1 hour, the mixture is warmed for a while so as to complete the reaction. After evaporation of the solvent, an aqueous solution of sodium bicarbonate is added to the residue to neutralize it. The mixture is then extracted with methylene chloride. The methylene chloride layer is washed with water and dried over sodium sulfate, followed by evaporation of the solvent. The residue is recrystallized from a mixture of acetone and n-hexane to give 8-chloro-6-phenyl-4H-s-triazolo [4,3-a][1,4] benzodiazepine as colorless flakes. Melting point; 226° C to 227° C.

Aufarbeitung

  1. additionTo the mixture is added dropwise
  2. stirringAfter stirring for a further 1 hour
  3. temperaturethe mixture is warmed for a while so as
  4. customthe reaction
  5. customAfter evaporation of the solvent
  6. additionan aqueous solution of sodium bicarbonate is added to the residue
  7. extractionThe mixture is then extracted with methylene chloride
  8. washThe methylene chloride layer is washed with water
  9. dry with materialdried over sodium sulfate
  10. customfollowed by evaporation of the solvent
  11. customThe residue is recrystallized from a mixture of acetone and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-90dc2169421a4860a727a7fea7cdd172
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04116956

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