Réaction #1005984

ord-1fc12bf65f814bf28a0763330ed57e9f

Équation de réaction

CN(CCCCN=[N+]=[N-])C(=O)n1cnc(-c2ccccc2)c1
compound 48
CN(CCCCN=[N+]=[N-])C(=O)n1cnc(-c2ccccc2)c1
N-(4-azidobutyl)-N-methyl-4-phenyl-1H-imidazole-1-carboxamide
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
S=C=S
Carbondisulfide
CN(CCCCN=C=S)C(=O)n1cnc(-c2ccccc2)c1
crude compound
CN(CCCCN=C=S)C(=O)n1cnc(-c2ccccc2)c1
N-(4-isothiocyanatobutyl)-N-methyl-4-phenyl-1H-imidazole-1-carboxamide

Solvants

Conditions de réaction

Température
50°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.WAITthe stirring continued at 50° C. for 4 h
  2. 2
    AutreReaction
  3. 3
    Températurewas cooled to r.t.
  4. 4
    Autresolvent was evaporated on Rotavapor

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09271962B2uspto-grants-2016_03