Hydrazinecarboxaldehyde → Estazolam

HRID 1288066

Reaktionsgleichung

Reaktionsgleichung von HRID 1288066
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[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.[CH:20]([NH:22][NH2:23])=O>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:20]=[N:22][N:23]=[C:10]3[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

4

Edukt 2

HCID 12229HydrazinecarboxaldehydeHCID 826706Thionordiazepam

Produkt 1

HCID 3261Estazolam

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 5.74 g. (0.020 mole) of 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione, 3.6 g. (0.060 mole) of formic acid hydrazide and 200 ml. of 1-butanol was refluxed for 3.75 hours with a slow stream of nitrogen bubbling through the mixture. The mixture was concentrated, the residue was suspended in water, and the suspension was filtered. The filter cake consisted principally of unchanged starting material. The filtrate was concentrated, ethyl acetate and Skellysolve B hexanes being added during the concentration, giving crude product (2.54 g.) of melting point 220.5°-225° C. Recrystallization of this material from ethyl acetate-Skellysolve B hexanes gave 8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of melting point 228°-229° C. The ultraviolet spectrum (ethanol) had end absorption λ max. 222 (ε = 40,950) and inflections at 245 (ε = 16,200) and 285 mμ(ε = 3,500).

Aufarbeitung

  1. additionA mixture of 5.74 g
  2. concentrationThe mixture was concentrated
  3. filtrationthe suspension was filtered
  4. concentrationThe filtrate was concentrated
  5. additionethyl acetate and Skellysolve B hexanes being added during the concentration
  6. customgiving crude product (2.54 g.) of melting point 220.5°-225° C
  7. customRecrystallization of this material from ethyl acetate-Skellysolve B hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c195d14230f8426daf2011c549160f8b
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03987052

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