Reaktionsgleichung
C(O[C:4]1[CH2:10][C:9](=[O:11])[NH:8][C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[N:5]=1)C.[C:16]([NH:24][NH2:25])(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(O)=O>[C:17]1([C:16]2[N:5]3[C:4]([CH2:10][C:9](=[O:11])[NH:8][C:7]4[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=43)=[N:25][N:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
To a solution of 4-ethoxy-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Preparation 3(A) (5 g, 24 mmol) in glacial AcOH (75 mL) was added benzoic acid hydrazide (3.33 g, 24.5 mmol). The reaction mixture was heated to 120° C. for 2 hours and was cooled to room temperature. The solvent was removed in vacuo by azeotropic distillation with heptane (2×). The residue was dissolved in a minimum amount of methylene chloride and 50 mL ethyl acetate and the solution was poured slowly with stirring into a solution of 100 mL saturated NaHCO3/100 mL water. Ether (150 mL) was added and the mixture was stirred for 5 minutes. The precipitate was collected by filtration, was washed with water and the minimum amount of ether to give 5.89 g of 1-phenyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one. 1H NMR (CDCl3) δ 9.02 (br s, 1H), 7.48-7.36 (m, 6H), 7.10 (t, 1H), 6.95 (d, 1H), 4.23 (d, 1H), 3.60 (d, 1H); MS 277 (M+1).
Aufarbeitung
- temperaturewas cooled to room temperature
- customThe solvent was removed in vacuo by azeotropic distillation with heptane (2×)
- dissolutionThe residue was dissolved in a minimum amount of methylene chloride and 50 mL ethyl acetate
- additionthe solution was poured slowly
- additionEther (150 mL) was added
- stirringthe mixture was stirred for 5 minutes
- filtrationThe precipitate was collected by filtration
- washwas washed with water
Quellen und Nachweise
- ORD-Eintrag
- ord-0bef033ef9d54ac8b6b7d255c5c2a60a
- Quelldatensatz
- uspto-grants-2007_09
- Patentnummer
- US07265104B2
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