Ethylene Glycol → 2-hydroxyethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

HRID 1447333

Reaktionsgleichung

Reaktionsgleichung von HRID 1447333
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:10]3[CH2:9][N:8]([CH3:20])[C:7](=[O:21])[C:6]=2[CH:22]=1.[C-]#N.[K+].C(O)C[OH:28]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][CH2:18][CH2:19][OH:28])=[O:16])=[C:10]3[CH2:9][N:8]([CH3:20])[C:7](=[O:21])[C:6]=2[CH:22]=1

Komponenten

4

Edukt 3

HCID 174Ethylene GlycolHCID 3373FlumazenilHCID 9032Potassium Cyanide

Produkt 1

HCID 205153142-hydroxyethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 6.08 g (20 mmol) of ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, 100 mg of potassium cyanide and 60 ml of ethyleneglycol is stirred at 130° C. for 6 hours and subsequently evaporated. After taking up the residue in chloroform, the solution is washed with water, dried over magnesium sulphate and evaporated. After recrystallisation of the crude product from ethyl acetate, there is obtained 2-hydroxyethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 202°-204° C.

Aufarbeitung

  1. customsubsequently evaporated
  2. washthe solution is washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customAfter recrystallisation of the crude product from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-995f75c66cb04658859a7b2659eea050
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04316839

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