Sodium amide → 7-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1606953
[Cl-].[Cl:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-].[Na+].[Cl:25][C:26]1[C:31]2[C:32](=[O:43])[N:33]([CH3:42])[CH2:34][C:35]3[N:36]([CH:37]=[N:38][C:39]=3[CH:40]=O)[C:30]=2[CH:29]=[CH:28][CH:27]=1>O1CCCC1>[Cl:25][C:26]1[C:31]2[C:32](=[O:43])[N:33]([CH3:42])[CH2:34][C:35]3[N:36]([CH:37]=[N:38][C:39]=3/[CH:40]=[CH:3]\[Cl:2])[C:30]=2[CH:29]=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 24533Sodium amideHCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 198515847-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde

Produkt 1

HCID 867433557-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

100 g of an equimolar mixture of chloromethyltriphenylphosphonium chloride and sodium amide were stirred for 45 minutes in 450 ml of tetrahydrofuran, whereby the temperature rose to 37°. 62.23 g (229.7 mmol) of 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde were then added portionwise thereto at room temperature and, after completion of the addition, the mixture was stirred for a further 1 hour. The reaction mixture was subsequently filtered and the filtrate was evaporated. After chromatography of the residue on silica gel while eluting with cyclohexane/ether/wasopropanol (3:3:1) there was obtained 7-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 205°-207°.

Aufarbeitung

  1. customrose to 37°
  2. additionat room temperature and, after completion of the addition
  3. filtrationThe reaction mixture was subsequently filtered
  4. customthe filtrate was evaporated
  5. washAfter chromatography of the residue on silica gel while eluting with cyclohexane/ether/wasopropanol (3:3:1) there

Quellen und Nachweise

ORD-Eintrag
ord-4e6d176c92604bb192e57a7ddecd8b8f
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04863920

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