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Ethanol → ethyl 2-amino-5-(4-benzyloxyphenyl)-1H-pyrrole-3-carboxylate

HRID 1433412
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1433412
C(O)C.Cl.[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[NH:7])[NH2:6].[O-]CC.[Na+].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=O)[CH2:33]Br)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[CH2:12]([O:11][C:9]([C:8]1[CH:33]=[C:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:27][CH:28]=2)[NH:7][C:5]=1[NH2:6])=[O:10])[CH3:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneHCID 15555354Ethyl 2-carbamimidoylacetate hydrochloride

Produkt 1

HCID 22936919ethyl 2-amino-5-(4-benzyloxyphenyl)-1H-pyrrole-3-carboxylateAusbeute 103,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

After adding 700 ml of ethanol to 50.7 g of ethyl 2-amidinoacetate hydrochloride (a publicly known compound described in Liebigs Ann. Chem., 1895 (1977)), the mixture was stirred at room temperature, 22.3 g of sodium ethoxide (1 equivalent with respect to ethyl 2-amidinoacetate hydrochloride) was added, and the mixture was stirred for 15 minutes under a nitrogen atmosphere. To this there was added 49.9 g of 1-(4-benzyloxyphenyl)-2-bromoethanone (publicly known compound described in Journal of Heterocyclic Chemistry, vol. 2, 310 (1965) and Journal of Medicinal Chemistry, vol. 17, 55 (1974)), and the mixture was stirred for 36 hours at room temperature under a nitrogen atmosphere. Water was added, ethyl acetate was used for liquid separation and extraction, and then the organic layer was dried over sodium sulfate and concentrated to dryness to obtain 56.7 g of the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred for 15 minutes under a nitrogen atmosphere
  2. stirringwas stirred for 36 hours at room temperature under a nitrogen atmosphere
  3. customethyl acetate was used for liquid separation and extraction
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-10abc7a78d78431793121f2304ef674a
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612092B2

Notizen zur Reaktion

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