Ethyl Acetate → 1-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one

HRID 914704

Reaktionsgleichung

Reaktionsgleichung von HRID 914704
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.[CH:16]1([C:22]([NH:24][NH2:25])=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C.CCOCC.O>[CH:16]1([C:22]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)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 240039CyclohexanecarbohydrazideHCID 516892Sodium BicarbonateHCID 589579152H-1,5-Benzodiazepin-2-one, 4-ethoxy-1,3-dihydro-

Produkt 1

HCID 589579321-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

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, 24.5 mmol) in glacial acetic acid (75 mL) was added cyclohexanecarboxylic acid hydrazide (Preparation 14) (3.5 g, 24.5 mmol). The reaction was heated at 120° C. for 2.5 hours, was cooled to room temperature, and EtOAc (50 mL), water (50 mL) and aqueous NaHCO3 (50 mL) were added. The mixture was stirred for 5 minutes and Et2O was added (125 mL). The suspension was stirred for 15 minutes and the solids were removed by filtration with the aid of Et2O to provide 5.92 g of 1-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one.

Aufarbeitung

  1. temperaturewas cooled to room temperature
  2. stirringThe suspension was stirred for 15 minutes
  3. customthe solids were removed by filtration with the aid of Et2O

Quellen und Nachweise

ORD-Eintrag
ord-9aba5b85b52e4d65a8a109a030e7cf10
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265104B2

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