Tetrahydrofuran → 7-chloro-4,5-dihydro-5-methyl-3-vinyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one
Reaktionsgleichung
[NH2-].[Na+].[Cl:3][C:4]1[C:9]2[C:10](=[O:21])[N:11]([CH3:20])[CH2:12][C:13]3[N:14]([CH:15]=[N:16][C:17]=3[CH:18]=O)[C:8]=2[CH:7]=[CH:6][CH:5]=1.O1CCC[CH2:23]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:3][C:4]1[C:9]2[C:10](=[O:21])[N:11]([CH3:20])[CH2:12][C:13]3[N:14]([CH:15]=[N:16][C:17]=3[CH:18]=[CH2:23])[C:8]=2[CH:7]=[CH:6][CH:5]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
6.25 g of an equimolar mixture of methyltriphenylphosphonium bromide and sodium amide was stirred for 15 minutes in 40 ml of tetrahydrofuran. 4.13 g (15 mmol) of 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde was then added to the yellow suspension, whereby the temperature rose to 43° and the suspension decolorized. The mixture was stirred for a further 1 hour, filtered and the filtrate was evaporated. After chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and recrystallization from ethyl acetate there was obtained 7-chloro-4,5-dihydro-5-methyl-3-vinyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 205°-207°.
Aufarbeitung
- customrose to 43°
- filtrationfiltered
- customthe filtrate was evaporated
- washAfter chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and recrystallization from ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-36e2cb02f40e43fdb7fee14d964432c4
- Quelldatensatz
- uspto-grants-1989_09
- Patentnummer
- US04863920
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