Réaction #67028

Équation de réaction

aminoguanidine hydrochloride

1-cyclopropyl-4-isothiocyanato naphthalene

diisopropylethylamine

→

5-amino-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazole-3-thiol

Rendement 50.6%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was removed under reduced pressure, toluene
2. 2
   workup.ADDITIONadded
3. 3
   Autrethe solvent was evaporated again
4. 4
   workup.ADDITIONSodium hydroxide solution (2M, 30 mL) was added
5. 5
   Températurethe reaction mixture heated at 50° C. for 60 hours
6. 6
   FiltrationThe reaction mixture was filtered
7. 7
   FiltrationThe mixture was re-filtered
8. 8
   Autrethe solvent removed under reduced pressure
9. 9
   AutreThe residue was purified by silica gel chromatography

Mode opératoire

A mixture of aminoguanidine hydrochloride (3.18 g, 29 mmol), 1-cyclopropyl-4-isothiocyanato naphthalene (3.24 g, 14 mmol) and diisopropylethylamine (3 eq) in DMF (20 mL) was stirred at 50° C. for 15 hours. The solvent was removed under reduced pressure, toluene added, and the solvent was evaporated again. Sodium hydroxide solution (2M, 30 mL) was added and the reaction mixture heated at 50° C. for 60 hours. The reaction mixture was filtered and the filtrate neutralized with aqueous HCl (2M). The mixture was re-filtered and the solvent removed under reduced pressure. The residue was purified by silica gel chromatography to yield 5-amino-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazole-3-thiol (2.0 g, 49%).

Source