N-{[5-(2-chloroacetyl)furan-2-yl]methyl}acetamide → 4-(5-Acetylaminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole

HRID 1033048

Reaktionsgleichung

Reaktionsgleichung von HRID 1033048
[C:1]([NH:4][CH2:5][C:6]1[O:10][C:9]([C:11](=O)[CH2:12]Cl)=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[NH2:15][C:16](=[N:18][C:19]([NH2:21])=[S:20])[NH2:17]>C(O)C>[C:1]([NH:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[N:21]=[C:19]([N:18]=[C:16]([NH2:17])[NH2:15])[S:20][CH:12]=2)=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 2393628N-{[5-(2-chloroacetyl)furan-2-yl]methyl}acetamideHCID 2724563Amidinothiourea

Produkt 1

HCID 117783664-(5-Acetylaminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazoleAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 5-acetylaminomethyl-2-chloroacetylfuran (39.9 g) and diaminomethylenethiourea (21.9 g) in ethanol (400 ml) was refluxed for two hours with stirring. The solvent was evaporated in vacuo and the residue was dissolved in water (300 ml). The solution was basified with an aqueous potassium carbonate. The resulting precipitate was collected by filtration, washed with water and recrystallized from a mixture of methanol, tetrahydrofuran and diisopropyl ether to afford 4-(5-acetylaminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (24.1 g).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in water (300 ml)
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customrecrystallized from a mixture of methanol, tetrahydrofuran and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8a22acb0dcf145649c406210ab4bf3a1
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05308857

Verknüpfte Notizen

Wird geladen…