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Benzamidine, hydrochloride → HCID 22386595, Verbindung

HRID 2121823
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2121823
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[C:4]#[N:5].Cl.[C:18]([NH2:26])(=[NH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])(=O)C.[Na+]>CN(C)C(=O)C>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[CH:7][C:6]=2[O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:26]=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 80289Benzamidine, hydrochlorideHCID 517045Sodium AcetateHCID 27374532-fluoro-6-phenoxybenzonitrile

Produkt 1

HCID 22386595HCID 22386595, VerbindungAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-fluoro-6-phenoxybenzonitrile (2.7 g, 13 mmol), benzamidine hydrochloride (Aldrich) (3.0 g, 19 mmol) and sodium acetate (1.6 g, 19 mmol) in 60 ml of N,N-dimethylacetamide was heated at 150° C. under nitrogen for 6.5 hours. After cooling to room temperature the reaction mixture was evaporated under reduced pressure. The product was suspended in 20 ml of ethanol and water (100 ml) and concentrated ammonium hydroxide (10 ml) was added. The precipitate was isolated by filtration, washed with water, dried and recrystallized twice from 60 ml of 2-propanol at 4° C. The precipitate was collected by filtration, washed with 2-propanol and dried at 50° C. in vacuo to give 4-amino-2-phenyl-5-phenoxyquinazoline (0.5 g, 12%, m.p. 190-191° C.):

Aufarbeitung

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas evaporated under reduced pressure
  3. additionwater (100 ml) and concentrated ammonium hydroxide (10 ml) was added
  4. customThe precipitate was isolated by filtration
  5. washwashed with water
  6. customdried
  7. customrecrystallized twice from 60 ml of 2-propanol at 4° C
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with 2-propanol
  10. customdried at 50° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e7493d85b9fc498a9a97e7630229fc07
Quelldatensatz
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06696482B2

Notizen zur Reaktion

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