Cyanoacetic acid hydrazide → HCID 12562505, Verbindung

HRID 597070

Reaktionsgleichung

Reaktionsgleichung von HRID 597070
[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.[C:20]([CH2:22][C:23]([NH:25][NH2:26])=O)#[N:21]>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:23]([CH2:22][C:20]#[N:21])=[N:25][N:26]=[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 8820Cyanoacetic acid hydrazideHCID 826706Thionordiazepam

Produkt 1

HCID 12562505HCID 12562505, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 1,3-dihydro-7-chloro-5-phenyl-2H-1,4-benzodiazepine-2-thione (5.72 g., 0.02 mole), cyanoacetic acid hydrazide (5.95 g., 0.06 mole) and n-butylalcohol (275 ml.) is refluxed for 7.5 hours with a slow stream of nitrogen bubbling through the mixture. The mixture is then concentrated in vacuo. The resulting residue is suspended in water and extracted with methylene chloride. The extract was dried and concentrated. The residue is chromatographed on silica gel (400 g.) with 2% methanol- 98% CHCl3. The product eluted from the column is crystallized from ethyl acetate-Skellysolve B hexanes to give 2.62 g. of 8-chloro-6-phenyl-4H-s-triazolo[4,3a][1,4]benzodiazepine-1-acetonitrile of melting point 198°-201° C.

Aufarbeitung

  1. temperatureis refluxed for 7.5 hours with a slow stream of nitrogen bubbling through the mixture
  2. concentrationThe mixture is then concentrated in vacuo
  3. extractionextracted with methylene chloride
  4. customThe extract was dried
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (400 g.) with 2% methanol- 98% CHCl3
  7. washThe product eluted from the column
  8. customis crystallized from ethyl acetate-Skellysolve B hexanes
  9. customto give 2.62 g

Quellen und Nachweise

ORD-Eintrag
ord-fdd650ad424349b2a7679bb70ae0f147
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04012413

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