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

HRID 361561노트

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HRID 361561 반응식
[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]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 123949352,3,9,10a-Tetrahydro-1H-benzo[b]cyclopenta[f][1,4]diazepin-10-one

생성물 1

HCID 701129649-(4-Nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one수율 70,993.102%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2e7bfb9c63364c5794aeae8941d31950
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866567

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