Reaction #1005984

Reaction equation

compound 48

N-(4-azidobutyl)-N-methyl-4-phenyl-1H-imidazole-1-carboxamide

triphenylphosphine

Carbondisulfide

→

crude compound

N-(4-isothiocyanatobutyl)-N-methyl-4-phenyl-1H-imidazole-1-carboxamide

Solvents

toluene

Conditions

Workup

1. 1
   workup.WAITthe stirring continued at 50° C. for 4 h
2. 2
   OtherReaction
3. 3
   Temperaturewas cooled to r.t.
4. 4
   Othersolvent was evaporated on Rotavapor

Procedure

To a compound 48 (0.85 mmol) in anhydrous toluene (20 mL) was added triphenylphosphine (1 mmol) and reaction mixture was stirred at 50° C. for 2 h. Carbondisulfide (10 mmol) was added and the stirring continued at 50° C. for 4 h. Reaction was cooled to r.t. and solvent was evaporated on Rotavapor to give a crude compound which on purification by Biotage SP1 gave a pure isothiocyante 49.

Source