Methyl iodide → cis-4,5-bis-(3-Fluorophenyl)-2-methylthio-4,5-dihydro-1H-imidazole hydroiodide

HRID 18714Notes

Reaction equation

HRID 18714 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[NH:11][C:10](=[S:20])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:21][I:22]>CCO>[IH:22].[F:19][C:15]1[CH:14]=[C:13]([C@H:12]2[C@@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[NH:9][C:10]([S:20][CH3:21])=[N:11]2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86596312cis-4,5-bis-(3-Fluorophenyl)imidazolidine-2-thione

Product 1

HCID 68570222cis-4,5-bis-(3-Fluorophenyl)-2-methylthio-4,5-dihydro-1H-imidazole hydroiodideYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cis-4,5-bis-(3-fluorophenyl)imidazolidine-2-thione (27) (4.5 g, 0.0188 mol) and methyl iodide (1.45 mL, 0.0232 mol) in abs. EtOH (50 mL) is heated at 95° C. overnight. The reaction mixture is cooled to RT, concentrated in vacuo, and the residue suspended in abs EtOH/Et2O. The insoluble material is filtered to give 6.10 g of the product 44. 1H NMR (DMSO-d6) δ 10.78 (s, 2 H), 7.30-7.15 (m, 2 H), 7.05-6.90 (m, 6 H); 5.87 (s, 2 H), 2.87 (s, 3 H); MS: m/z 305 (M++1).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationThe insoluble material is filtered

Sources & evidence

ORD record
ord-9100e9652578438fa51396f96d6ac011
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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