Sodium hydride → 9-(4-Nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 361561

Reaktionsgleichung

[CH2:1]1[CH:10]2[C:4](=[N:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9]2=[O:11])[CH2:3][CH2:2]1.[H-].[Na+].[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)([O-:20])=[O:19]>CN(C)C=O.[Cl-].[NH4+]>[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:8]2[C:9](=[O:11])[CH:10]3[CH2:1][CH2:2][CH2:3][C:4]3=[N:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]2=3)=[CH:23][CH:22]=1)([O-:20])=[O:19]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A suspension of 2,3,9,10a-tetrahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one (25.00 g, 0.125 mmol) in N,N-dimethylformamide (DMF) (150 mL) was cooled to 0° C. and sodium hydride (60% dispersion in liquid paraffin, 5.00 g, 0.125 mol) was added. The mixture was stirred at the same temperature for 10 minutes and then at 20° C. for 5 minutes. After the resulting solution was cooled to 0° C., 4-nitrobenzyl bromide (28.32 g, 0.131 mol) was added and the mixture was stirred at 20° C. for 10 minutes. This reaction mixture was poured in saturated aqueous ammonium chloride solution (500 mL) and the resulting precipitate was recovered by filtration, rinsed with water, and recrystallized from dichloromethane-ethanol to provide 29.76 g (yield 71%) of the title compound. Samples for analysis were recrystallized from chloroform-ethanol. m.p. 185°-188° C.

Aufarbeitung

waitat 20° C. for 5 minutes
temperatureAfter the resulting solution was cooled to 0° C.
stirringthe mixture was stirred at 20° C. for 10 minutes
filtrationthe resulting precipitate was recovered by filtration
washrinsed with water
customrecrystallized from dichloromethane-ethanol

Quellen und Nachweise

ORD-Eintrag: ord-2e7bfb9c63364c5794aeae8941d31950
Quelldatensatz: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05866567

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