Dimethylformamide → [1,1'-Biphenyl]-4-yl-(5-methyl-5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanone

HRID 1354024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354024
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[O:8])=[CH:3][CH:2]=1.[H-].[Na+].[CH3:32]N(C)C=O>[Cl-].[Na+].O>[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[N:12]([CH3:32])[C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[O:8])=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 9821040[1,1'-Biphenyl]-4-yl-(5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanone

Produkt 1

HCID 10110970[1,1'-Biphenyl]-4-yl-(5-methyl-5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

[1,1′-Biphenyl]-4-yl-(5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanone of Example 6 (0.97 g) was added to sodium hydride (2 equivalents, 60% in oil, washed with hexane) and N,N-dimethylformamide (25 mL). lodomethane (0.45 g) was added and after overnight stirring, the mixture was poured into brine. The precipitate was collected, redissolved in dichloromethane and the solution filtered through a short column of Magnesol®. The column was rinsed with several volumes of dichloromethane, and the combined eluate refluxed with the gradual addition of hexane until incipient crystallization. Cooling and filtration provided the title compound (0.89 g), m.p. 198–201° C.

Aufarbeitung

  1. additionlodomethane (0.45 g) was added and after overnight
  2. customThe precipitate was collected
  3. dissolutionredissolved in dichloromethane
  4. filtrationthe solution filtered through a short column of Magnesol®
  5. washThe column was rinsed with several volumes of dichloromethane
  6. temperaturethe combined eluate refluxed with the gradual addition of hexane until incipient crystallization
  7. temperatureCooling
  8. filtrationfiltration

Quellen und Nachweise

ORD-Eintrag
ord-41a510efe40e42f8971f0d4cbfd8ef23
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223752B2

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