Cyanide → 6-cyano-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione

HRID 1252672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1252672
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[C:10](Br)=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:15])[CH2:3]1.[C-:16]#[N:17].[Na]>CN(C)C=O.O>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[C:10]([C:16]#[N:17])=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:15])[CH2:3]1

Komponenten

6

Edukt 3

HCID 5975CyanideHCID 5360545SodiumHCID 199051123,4-dihydro-4-methyl-6-bromo-2H-1,4-benzodiazepine-2,5(1H)-dione

Produkt 1

HCID 201389616-cyano-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dioneAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2.3 g of 3,4-dihydro-4-methyl-6-bromo-2H-1,4-benzodiazepine-2,5(1H)-dione (U.S. Pat. No. 4,352,817 ex.9) and 1.26 g of cupro cyanide was dissolved in 5 ml dimethyl formamide. This mixture was heated to 110° C. for 30 minutes. This mixture was then cooled to 50° C. and 2.4 g sodium in 6 ml water was added. The resulting mixture was then stirred for 10 minutes, whereafter 30 ml water was added. This mixture was extracted two times with 25 ml ethyl acetate. The organic phase was dryed with calcium chloride. After filtration the organic solution was evaporated in vacuo to give 0.78 g of the title compound. M.p. 261°-69° C.

Aufarbeitung

  1. temperatureThis mixture was then cooled to 50° C.
  2. extractionThis mixture was extracted two times with 25 ml ethyl acetate
  3. filtrationAfter filtration the organic solution
  4. customwas evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-459d66bb8b9840b7ada7ba9a55832fb2
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04745112

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