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Dimethylformamide → 4-[[4-(Aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid

HRID 1735627
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1735627
Cl.Cl.[NH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=N)=[CH:6][CH:5]=1.C[N:14](C=O)C.[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1.CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[NH2:14][N:10]=[CH:8][C:7]1[CH:6]=[CH:5][C:4]([NH:3][C:18](=[O:24])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:12][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 756264-Amidinoaniline dihydrochloride

Produkt 1

HCID 699510564-[[4-(Aminoiminomethyl)phenyl]amino]-4-oxobutanoic acidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049
Pyridine
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

U.S. Pat. No. 5,344,957 discloses a process for preparing ethyl 3S 3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-4-pentynoate having the following formula ##STR2## This process is described as follows: 4-Aminobenzamidine di-HCl (25 g, 120 mmol), which is commercially available, particularly from Aldrich, was added to dry DMF (100 ml). To this solution dry pyridine (100 ml) and succinic anhydride (12 g, 120 mmol) followed by dimethylaminopyridine (DMAP 1.5 g 0.012 mmol) were added. The product precipitated after heating for 1/2 h at 100° C. The product was filtered, washed with water, acetonitrile and ether. The light solid was suspended in dioxane, 4N HCl in dioxane (100 ml) was added and the suspension was stirred for 1 h, filtered and dried in a desiccator to give 28 g, 88% of 4-[[4-(aminoiminomethyl)phenyl]-amino]-4-oxobutanoic acid as a white yellow solid which decomposes between 270° C. and 290° C.

Aufarbeitung

  1. additionwere added
  2. customThe product precipitated
  3. filtrationThe product was filtered
  4. washwashed with water, acetonitrile and ether
  5. addition4N HCl in dioxane (100 ml) was added
  6. filtrationfiltered
  7. customdried in a desiccator

Quellen und Nachweise

ORD-Eintrag
ord-562f7e6e215542c0ac1646e171e934b3
Quelldatensatz
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05536869

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