Triethylamine → 4-{N'-[2-(4-Nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carbonyl]-hydrazino}-butyric acid ethyl ester

HRID 1713052

Reaktionsgleichung

Reaktionsgleichung von HRID 1713052
C(O[C:4]([C:6]1[NH:10][C:9]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[O:13][C:8]=2[CH:7]=1)=[O:5])C.[NH2:23][NH2:24].Br[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(N(CC)CC)C>CC(O)C>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][NH:23][NH:24][C:4]([C:6]1[NH:10][C:9]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)[O:13][C:8]=2[CH:7]=1)=[O:5])[CH3:33]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9321HydrazineHCID 76300Ethyl 4-bromobutyrateHCID 594634452-(4-nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester

Produkt 1

HCID 594634534-{N'-[2-(4-Nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carbonyl]-hydrazino}-butyric acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

As depicted in Scheme 31 below, 2-(4-nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester (0.1 mmol) is dissolved in 2-propanol (10 ml) and hydrazine (0.11 mmol) is added. The resulting mixture is heated at 80° C., while monitoring the reaction progress by TLC. Once the reaction is completed (the starting material is no longer detected), the solvents are evaporated under reduced pressure, dioxane (20 ml) is added to the crude mixture, followed by addition of ethyl 4-bromobutyrate (0.1 mmol) and triethylamine (0.1 mmol), and the resulting mixture is heated to reflux, while monitoring the reaction progress by TLC. Once the reaction is completed (the starting material is no longer detected), the solvent is evaporated, and a mixture of ethyl acetate and water is added. The phases are separated, and the aqueous phase is extracted with ethyl acetate. The combined organic phase is dried over Na2SO4, and the solvents are evaporated under reduced pressure to give crude 4-{N′-[2-(4-Nitro-phenyl)-4H-furo[3,2-b]pyrrole-5-carbonyl]-hydrazino}-butyric acid ethyl ester which is purified by column chromatography.

Aufarbeitung

  1. customare evaporated under reduced pressure, dioxane (20 ml)
  2. additionis added to the crude mixture
  3. temperaturethe resulting mixture is heated
  4. temperatureto reflux
  5. customis evaporated
  6. additiona mixture of ethyl acetate and water
  7. additionis added
  8. customThe phases are separated
  9. extractionthe aqueous phase is extracted with ethyl acetate
  10. dry with materialThe combined organic phase is dried over Na2SO4
  11. customthe solvents are evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-970caa5248cd4993a821dc3b97c61455
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795255B2

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