Reaktion #1579036

Reaktionsgleichung

2-(acetylaminomethyl)-6-bromoacetylpyridine

diaminomethylenethiourea

→

4-(6-acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole

Ausbeute 49.8%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed by concentration in vacuo
2. 2
   workup.ADDITIONTo the residue was added
3. 3
   workup.ADDITIONa mixture of water, ethyl acetate and tetrahydrofuran
4. 4
   WaschenThe separated organic layer was washed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   SonstigeEvaporation of the solvent
7. 7
   Sonstigegave a residue, which
8. 8
   Sonstigewas purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (85:15, V/V)
9. 9
   workup.ADDITIONThe eluted fractions containing the desired product
10. 10
    Sonstigewere collected
11. 11
    Sonstigeevaporated in vacuo
12. 12
    SonstigeThe residue was triturated with a mixture of ethyl acetate and diisopropyl ether

Vorschrift

A mixture of 2-(acetylaminomethyl)-6-bromoacetylpyridine (50.0 g) and diaminomethylenethiourea (15.3 g) in ethanol (400 ml) was stirred at 40° to 50° C. for 2 hours. The solvent was removed by concentration in vacuo. To the residue was added a mixture of water, ethyl acetate and tetrahydrofuran, and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (85:15, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was triturated with a mixture of ethyl acetate and diisopropyl ether to give 4-(6-acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (18.73 g).

Quelle