Methyl iodide → cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-1H-imidazole hydroiodide

HRID 18712

Reaction equation

HRID 18712 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:10][C:9](=[S:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][I:20]>CCO>[IH:20].[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:10][C:9]([S:18][CH3:19])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 68569083cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-1H-imidazole hydroiodideYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationThe insoluble material is filtered
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-e16fa8838a72498f8e3274390ac3c80c
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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