Réaction #46990

ord-e16fa8838a72498f8e3274390ac3c80c

Équation de réaction

S=C1N[C@H](c2ccccc2)[C@H](c2ccccc2)N1
cis-4,5-diphenylimidazolidine-2-thione
S=C1N[C@H](c2ccccc2)[C@H](c2ccccc2)N1
cis-4,5-Diphenylimidazolidine-2-thione
CI
methyl iodide
→
CSC1=N[C@@H](c2ccccc2)[C@@H](c2ccccc2)N1.I
product 42
Rendement 98.0%
CSC1=N[C@@H](c2ccccc2)[C@@H](c2ccccc2)N1.I
cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-1H-imidazole hydroiodide
Rendement 98.0%

Réactifs

S=C1N[C@H](c2ccccc2)[C@H](c2ccccc2)N1
cis-4,5-diphenylimidazolidine-2-thione
S=C1N[C@H](c2ccccc2)[C@H](c2ccccc2)N1
cis-4,5-Diphenylimidazolidine-2-thione
CI
methyl iodide

Réactifs

Aucun

Solvants

CCO
EtOH

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Concentrationconcentrated in vacuo
  2. 2
    FiltrationThe insoluble material is filtered
  3. 3
    Lavagewashed with Et2O

Mode opératoire

A mixture of cis-4,5-diphenylimidazolidine-2-thione (25) (58.16 g, 0.229 mol) and methyl iodide (35.6 mL, 0.87 mol) in abs. EtOH (500 mL) is heated at 95° C. overnight. The reaction mixture is cooled to RT, concentrated in vacuo, and the residue suspended in Et2O. The insoluble material is filtered, washed with Et2O to give 88.9 g of the product 42. 1H NMR (DMSO-d6) δ 10.75 (s, 2 H), 7.25-6.95 (m, 10 H), 5.85 (s, 2 H), 2.82 (s, 3H); MS: m/z 269 (M++1).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07741493B2uspto-grants-2010_06