O-Phenylenediamine → 2H-1,5-Benzodiazepin-2-one, 4-ethoxy-1,3-dihydro-

HRID 900123

Reaktionsgleichung

Reaktionsgleichung von HRID 900123
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH2:9]([O:11][C:12](=O)[CH:13]=[C:14](OCC)[O:15]CC)[CH3:10]>C(O)(=O)C>[CH2:9]([O:11][C:12]1[CH2:13][C:14](=[O:15])[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1)[CH3:10]

Komponenten

4

Edukt 2

HCID 7243O-PhenylenediamineHCID 1693882-Propenoic acid, 3,3-diethoxy-, ethyl ester

Produkt 1

HCID 589579152H-1,5-Benzodiazepin-2-one, 4-ethoxy-1,3-dihydro-Ausbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution phenylenediamine (17.2 g, 159.2 mmol) and acetic acid (0.4 mL) in xylenes (225 mL) at 140° C. was added 3,3-diethoxyacrylic acid ethyl ester (30.0 g, 159.2 mmol) in xylenes (80 mL) dropwise over 50 minutes. The reaction was heated at 140° C. for 2 hours, was cooled to room temperature, and was stirred for 24 h. The resulting white precipitate was filtered, was washed with ether (100 mL), and was dried under vacuum to provide 18.37 g of 4-ethoxy-1,3-dihydro-benzo[b][1,4]diazepin-2-one as a white fluffy solid. MS 205 (M+1).

Aufarbeitung

  1. temperaturewas cooled to room temperature
  2. filtrationThe resulting white precipitate was filtered
  3. washwas washed with ether (100 mL)
  4. customwas dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5027b21bf47241a689e990713549e76f
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358242B2

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