Methyl iodide → 1-(10,11-Dihydro-5-methyl-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone

HRID 2054142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2054142
[CH:1]1[C:11]2[CH2:10][N:9]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[C:8]3[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:25]>CN(C)C=O>[CH3:25][N:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[CH2:10][N:9]([C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]1=2

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 221352391-(10,11-Dihydro-5H-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone

Produkt 1

HCID 221352361-(10,11-Dihydro-5-methyl-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(10,11-Dihydro-5H-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone of Step A (3.12 g) was added to dry N,N-dimethylformamide (50 mL) containing sodium hydride (60% dispersion in oil, 0.60 g, washed with hexane). After a short while iodomethane was added (2.0 g) and the mixture stirred overnight at room temperature, quenched with ice and diluted with brine. The precipitate was collected and redissolved in dichloromethane. The solution was dried over anhydrous sodium sulfate and filtered through a short column of Magnesol® which was eluted with several additional volumes of dichloromethane. The total effluent was evaporated to dryness and the residue crystallized from hexane to provide the title compound as colorless crystals (1.23 g), m.p. 104-106° C.

Aufarbeitung

  1. customquenched with ice
  2. additiondiluted with brine
  3. customThe precipitate was collected
  4. dissolutionredissolved in dichloromethane
  5. dry with materialThe solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered through a short column of Magnesol® which
  7. washwas eluted with several additional volumes of dichloromethane
  8. customThe total effluent was evaporated to dryness
  9. customthe residue crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-362a401724fc421fa8cf88d03438383a
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07329653B2

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