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

HRID 2053508Notes

Reaction equation

HRID 2053508 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[NH:11][C:10](=[S:20])[NH:9]2)=[CH:4][CH:3]=1.[CH3:21][I:22]>CCO>[IH:22].[F:19][C:16]1[CH:17]=[CH:18][C:13]([C@H:12]2[C@@H:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[NH:9][C:10]([S:20][CH3:21])=[N:11]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86596313cis-4,5-bis-(4-Fluorophenyl)imidazolidine-2-thione

Product 1

HCID 68567000cis-4,5-bis-(4-Fluorophenyl)-2-methylthio-4,5-dihydro-1H-imidazole hydroiodideYield 936.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of cis-4,5-bis-(4-fluorophenyl)imidazolidine-2-thione (28) (1.78 g, 0.61 mmol) and methyl iodide (0.620 g, 10.0 mmol) in abs. EtOH (30 mL) is heated at 95° C. for 26 h. 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 2.47 g of the product 45. 1H NMR (DMSO-d6) δ 10.75 (s, 2H), 7.15-6.95 (m, 8H), 5.83 (s, 2H), 2.81 (s, 3H); MS: m/z 305 (M++1).

Workup

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

Sources & evidence

ORD record
ord-67e71f86f6444c3eafa58ee8d89011e8
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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