Methyl iodide → 11H-Dibenzo(b,e)(1,4)diazepin-11-one, 5,10-dihydro-10-methyl-

HRID 1378422

Reaktionsgleichung

Reaktionsgleichung von HRID 1378422
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[H-].[Na+].I[CH3:20]>CN(C)C=O>[CH3:20][N:8]1[C:2](=[O:1])[C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=2[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]1=2

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2013275,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-one

Produkt 1

HCID 3604211H-Dibenzo(b,e)(1,4)diazepin-11-one, 5,10-dihydro-10-methyl-Ausbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine (10 g, 0.048 mol, Synthesis, (1985), 550) in dry dimethylformamide (100 ml) kept under an atmosphere of nitrogen, sodium hydride (2.1 g, 0.052 mol, 60% dispersion in oil) was added, and the reaction mixture was stirred for 1.5 h. Iodomethane (3.27 ml, 0.052 mol) was slowly added keeping the temperature below 30° C. and the mixture was stirred overnight. The reaction mixture was quenched with saturated ammonium chloride (20 ml) and poured onto ice water (300 ml). The solid was filtered off and washed with plenty of water and dried. This yielded 10.4 g of crude 10-methyl-11-oxo-10,11-dihydro-5H-dibenzo [b,e][1,4]diazepine which was recrystallised from methanol (200 ml), to give 6.7 g (63%) of 10-methyl-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine. M.p. 210°-211° C.

Aufarbeitung

  1. customthe temperature below 30° C.
  2. stirringthe mixture was stirred overnight
  3. customThe reaction mixture was quenched with saturated ammonium chloride (20 ml)
  4. additionpoured onto ice water (300 ml)
  5. filtrationThe solid was filtered off
  6. washwashed with plenty of water
  7. customdried
  8. customThis yielded 10.4 g of crude 10-methyl-11-oxo-10,11-dihydro-5H-dibenzo [b,e][1,4]diazepine which was recrystallised from methanol (200 ml)

Quellen und Nachweise

ORD-Eintrag
ord-979100446f7443719b2bd2d27ed225ff
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668129

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