Reaktion #1120230

ord-8a22acb0dcf145649c406210ab4bf3a1

Reaktionsgleichung

CC(=O)NCc1ccc(C(=O)CCl)o1
5-acetylaminomethyl-2-chloroacetylfuran
NC(=S)N=C(N)N
diaminomethylenethiourea
CC(=O)NCc1ccc(-c2csc(N=C(N)N)n2)o1
4-(5-acetylaminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole
Ausbeute 46.6%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvent was evaporated in vacuo
  2. 2
    workup.DISSOLUTIONthe residue was dissolved in water (300 ml)
  3. 3
    FiltrationThe resulting precipitate was collected by filtration
  4. 4
    Waschenwashed with water
  5. 5
    Sonstigerecrystallized from a mixture of methanol, tetrahydrofuran and diisopropyl ether

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05308857uspto-grants-1994_05