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Ethanol → Ethyl (4-acetyl-2-nitrophenyl)aminobenzoate

HRID 49826
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 49826
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)=[O:3].N[C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19].C([N:28](CC)CC)C.C(O)C>CN1C(=O)CCC1>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:28][C:23]2[CH:24]=[CH:25][CH:15]=[CH:16][C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)(=[O:3])[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 27346124'-Fluoro-3'-nitroacetophenone

Produkt 1

HCID 53953856Ethyl (4-acetyl-2-nitrophenyl)aminobenzoateAusbeute 938,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Versuchsvorschrift

A mixture 1b (11.0 g, 60.2 mmol), ethyl 3-aminobenzoate (9.9 g, 6.2 mmol) and triethylamine (8.34 ml, 60.2 mmol) in anhydrous NMP (5 ml) was heated to 130° C. with stirring under a stream of nitrogen for 4 hours. The cooled mixture was poured into ice-water (100 ml). Ethanol (10 ml) was added and the mixture was stirred until crystallization was completed. The precipitate was filtered off, washed with water and dried to yield ethyl (4-acetyl-2-nitrophenyl)aminobenzoate (19.1 g, 97%). This ester was hydrogenated quantitatively in a mixture of ethanol (400 ml) and dichloromethane (100 ml) using Pd (5% on activated carbon) as the catalyst. The resulting diamine was heated to reflux in formic acid (100 ml) for 1 hour. The cooled mixture was poured into ice-water (400 ml) and the precipitate was filtered off, washed with water and dried to yield 5-acetyl-1-(3-ethoxycarbonyl)phenylbenzimidazole (16.4 g, 91%).

Aufarbeitung

  1. stirringthe mixture was stirred until crystallization
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-624de12a3733497c8932b4e4bb825d7e
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06710044B2

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