Reaktion #46995

ord-3f8900a5f4494265aaebccd7206614ab

Reaktionsgleichung

Cc1cccc([C@H]2NC(=S)N[C@H]2c2cccc(C)c2)c1
cis-4,5-bis-(3-methylphenyl)imidazolidine-2-thione
Cc1cccc([C@H]2NC(=S)N[C@H]2c2cccc(C)c2)c1
cis-4,5-bis-(3-Methylphenyl)imidazolidine-2-thione
CI
methyl iodide
→
CSC1=N[C@@H](c2cccc(C)c2)[C@@H](c2cccc(C)c2)N1.I
product 47
Ausbeute 92.5%
CSC1=N[C@@H](c2cccc(C)c2)[C@@H](c2cccc(C)c2)N1.I
cis-4,5-bis-(3-Methylphenyl)-2-methylthio-4,5-dihydro-1H-imidazole hydroiodide
Ausbeute 92.5%

Edukte

Cc1cccc([C@H]2NC(=S)N[C@H]2c2cccc(C)c2)c1
cis-4,5-bis-(3-methylphenyl)imidazolidine-2-thione
Cc1cccc([C@H]2NC(=S)N[C@H]2c2cccc(C)c2)c1
cis-4,5-bis-(3-Methylphenyl)imidazolidine-2-thione
CI
methyl iodide

Reagenzien

Keine

Lösungsmittel

CCO
EtOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated in vacuo
  2. 2
    FiltrationThe insoluble material is filtered

Vorschrift

A mixture of cis-4,5-bis-(3-methylphenyl)imidazolidine-2-thione (30) (2.23 g, 0.00825 mol) and methyl iodide (0.77 mL, 0.0124 mol) in abs. EtOH (30 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 to give 3.24 g of the product 47. 1H NMR (DMSO-d6) δ 10.71 (s, 2 H), 7.10-7.00 (m, 2 H), 7.00-6.90 (m, 2 H), 6.90-6.75 (m, 4 H), 5.73 (s, 2 H), 2.80 (s, 3 H), 2.13 (s, 6 H); MS: m/z 297 (M++1).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07741493B2uspto-grants-2010_06