Methyl iodide → HCID 13116872, compound

HRID 1701838Notes

Reaction equation

HRID 1701838 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([SH:20])=[N:9]2)=[CH:4][CH:3]=1.[CH3:21]I>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([S:20][CH3:21])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178527834HCID 178527834, compound

Product 1

HCID 13116872HCID 13116872, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.0 g of 4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazole-2-thiol, 4.0 g of methyl iodide and 100 ml of ethanol was heated at reflux for 4 hours. The solvent was removed in vacuo and the residue distributed between methylene chloride and 10% aqueous NaHCO3 solution. The organic layer was dried and evaporated to give 8.8 g of 4,5-bis(4-chlorophenyl)-4,5-dihydro-2-(methylthio)-1H-imidazole as a colorless oil. The NMR spectrum was consistent with this structure. The hydrochloride salt was prepared with dry hydrogen chloride gas in ether to give the title compound as colorless crystals (5.3 g), m.p. 236° dec.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was removed in vacuo
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-d9c2fa1c46424a02b3055f6767a97e5f
Source dataset
uspto-grants-1983_04
Patent number
US04379159

Reaction notes

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