Reaction #77549

Reaction equation

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

Solvents

THF

THF

Conditions

Workup

1. 1
   OtherThe product was precipitated from ether
2. 2
   Otherto form the white solid
3. 3
   OtherThe solid thus obtained
4. 4
   Washwas washed sequentially with ether, methanol and acetone

Procedure

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