Methyl iodide → HCID 68570732, compound

HRID 18718Notes

Reaction equation

HRID 18718 reaction equation
[CH3:1][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]([CH3:19])=[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].[CH3:19][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]([CH3:1])=[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 86596316HCID 86596316, compound

Product 1

HCID 68570732HCID 68570732, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cis-4,5-bis-(4-methylphenyl)imidazolidine-2-thione (31) (5.2 g, 0.0184 mol) and methyl iodide (1.72 mL, 0.0276 mol) in abs. EtOH (30 mL) is heated at 90° 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 7.56 g of the product 48. 1H NMR (DMSO-d6) δ 10.68 (s, 2 H), 7.00-6.85 (m, 8 H), 5.72 (s, 2 H), 2.79 (s, 3 H), 2.15 (s, 6 H); MS: m/z 297 (M++1).

Workup

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

Sources & evidence

ORD record
ord-22523c0340a844219022c8b159fb040c
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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