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

HRID 1354023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354023
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[CH:16]1[C:26]2[CH2:25][NH:24][C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[NH:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.O.ClCCl>CN(C)C=O>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([N:24]2[CH2:25][C:26]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[NH:21][C:22]3[CH:30]=[CH:29][CH:28]=[CH:27][C:23]2=3)=[O:8])=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 3604610,11-Dihydro-5h-dibenzo[b,e][1,4]diazepineHCID 841514-Phenylbenzoyl chloride

Produkt 1

HCID 9821040[1,1'-Biphenyl]-4-yl-(5,11-dihydro-10H-dibenzo[b,e][1,4]diazepin-10-yl)methanoneAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

4-Biphenyl-carbonyl chloride (1.19 g) dissolved in N,N-dimethylformamide (10 mL) was added dropwise to an ice cooled solution of 5,11-dihydro-10H-dibenzo[b,e][1,4]diazepine (0.98 g) in N,N-dimethylformamide (10 mL). After stirring at room temperature overnight, the reaction mixture was poured into water and dichloromethane. The organic layer was sequentially washed with water and saturated sodium bicarbonate, and dried over anhydrous sodium sulfate. The solution was filtered through a short column of Magnesol® and eluted with additional dichloromethane. The combined eluate was refluxed with gradual addition of hexane until incipient crystallization occurred. Cooling and filtration provided the title compound (0.72 g), m.p. 180–182° C.

Aufarbeitung

  1. washThe organic layer was sequentially washed with water and saturated sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solution was filtered through a short column of Magnesol®
  4. washeluted with additional dichloromethane
  5. temperatureThe combined eluate was refluxed with gradual addition of hexane until incipient crystallization
  6. temperatureCooling
  7. filtrationfiltration

Quellen und Nachweise

ORD-Eintrag
ord-99cf32bbe09149de9fdbdaddf6d43e28
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223752B2

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