Réaction #77549

Équation de réaction

N-(2-phenyl-2-hydroxyethyl)-N′-cyano-N″-4-pyridylguanidine

triphenylphosphine

diisopropyl azodicarboxylate

→

Compound 14

[5-phenyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]aminomethane-nitrile

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   AutreThe product was precipitated from ether
2. 2
   Autreto form the white solid
3. 3
   AutreThe solid thus obtained
4. 4
   Lavagewas washed sequentially with ether, methanol and acetone

Mode opératoire

To a solution of N-(2-phenyl-2-hydroxyethyl)-N′-cyano-N″-4-pyridylguanidine (1.0 g, 3.56 mmol) and triphenylphosphine (1.86 g, 7.12 mmol) in THF (30 mL) at 0° C. was added diisopropyl azodicarboxylate (3.8 mL, 7.12 mmol) dissolved in 15 mL (THF) by syringe pump over 30 min. The resulting mixture was kept stirring and warmed to room temperature for 70 h. The product was precipitated from ether to form the white solid. The solid thus obtained was washed sequentially with ether, methanol and acetone to give the product (i.e., Compound 14) as a white solid (0.67 g, 72%).

Source