Hydrazinecarboxylic acid, ethyl ester → 6-Ethyl-5-(2-phenyl-benzoxazol-6-yl)-3,6-dihydro-[1.3.4]oxadiazin-2-one

HRID 1619961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619961
[OH:1][CH:2]([CH2:20][CH3:21])[C:3]([C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:11][C:7]=2[CH:6]=1)=O.[NH:22]([C:24](OCC)=[O:25])[NH2:23].[Na]>Cl.C(O)C>[CH2:20]([CH:2]1[O:1][C:24](=[O:25])[NH:22][N:23]=[C:3]1[C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:11][C:7]=2[CH:6]=1)[CH3:21]

Komponenten

6

Edukt 3

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 5360545SodiumHCID 674627762-Hydroxy-1-(2-phenyl-benzoxazol-6-yl)-butan-1-one

Produkt 1

HCID 674645236-Ethyl-5-(2-phenyl-benzoxazol-6-yl)-3,6-dihydro-[1.3.4]oxadiazin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 702EthanolLösungsmittel3×

Versuchsvorschrift

50 mg (178 μmol) 2-hydroxy-1-(2-phenyl-benzoxazol-6-yl)-butan-1-one are refluxed together with 20.36 mg (196 μmol) ethyl hydrazinoformate, 1 drop of 0.1N hydrochloric acid and 500 μl ethanol for 10 min, then the solvent is completely removed i. V. The residue is dissolved in 2 ml dry ethanol. 40 mg (1740 μmol) sodium are dissolved in 1.2 ml dry ethanol and added dropwise to the first solution, the mixture is stirred overnight at RT, then separated by RP-HPLC.

Aufarbeitung

  1. additionadded dropwise to the first solution
  2. customseparated by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b52039f514be4f0c96c55fe171f7369b
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772323B2

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