Heptanoic Acid → Heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amide

HRID 47827

Reaktionsgleichung

Reaktionsgleichung von HRID 47827
Cl.CN(C)CCCN=C=NCC.[C:13]([OH:21])(=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30][NH2:31])=[CH:27][CH:26]=1)([O-:24])=[O:23].C(N(CC)CC)C>C(OCC)(=O)C.C(Cl)Cl>[N+:22]([C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH2:30][NH:31][C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:32][CH:33]=1)([O-:24])=[O:23]

Komponenten

7

Edukt 4

HCID 8094Heptanoic AcidHCID 8471TriethylamineHCID 951534-NitrophenethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 86586370Heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amideAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.86 g, 20.1 mmol) and heptanoic acid (2.38 mL, 16.8 mmol) were added sequentially to a solution of 4-nitrophenethylamine (3.40 g, 16.8 mmol), triethylamine (2.81 mL, 20.1 mmol) and methylene chloride (25 mL). After stirring 18 h at ambient temperature, the reaction mixture was diluted with ethyl acetate; washed sequentially with water, 1N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride; dried over anhydrous sodium sulfate; filtered and concentrated under reduced pressure to provide 3.80 g (81%) of heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amide as an off-white solid.

Aufarbeitung

  1. washwashed sequentially with water, 1N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a111074eabfd4a1fb8dcd2b34b409831
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699904B2

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