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

HRID 356144Notes

Reaction equation

[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].[Cl-].[NH4+]>CN(C)C=O>[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]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (25.00 g, 0.125 mol.) in N,N-dimethylformamide (150 mL) was cooled to 0° C., to which was added sodium hydride (60% liquid paraffin dispersion, 5.00 g, 0.125 mol.). This mixture was stirred for 10 minutes at the same temperature and for 5 minutes at 20° C. This solution was cooled to 0° C., to which was added 4-nitrobenzyl bromide (28.32 g, 0.131 mol.), and the mixture was stirred for 10 minutes at 20° C. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride (500 mL). Resulting precipitate was subjected to filtration, and washed with water, followed by recrystallization from dichloromethane-ethanol to give 29.76 g (yield 71%) of the titled compound. The sample for analylical experiment was prepared by recrystallization of the compound from chloroform-ethanol, m.p. 185°-188° C.

Workup

temperatureThis solution was cooled to 0° C., to which
stirringthe mixture was stirred for 10 minutes at 20° C
customResulting precipitate
filtrationwas subjected to filtration
washwashed with water
customfollowed by recrystallization from dichloromethane-ethanol

Sources & evidence

ORD record: ord-986ae27d19904754ad8ec8c82ad9b3f0
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834463

Reaction notes

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