Methyl iodide → HCID 68569174, compound

HRID 18717Notes

Reaction equation

HRID 18717 reaction equation
[CH3:1][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]([CH3:19])[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].[CH3:19][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]([CH3:1])[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 86596315HCID 86596315, compound

Product 1

HCID 68569174HCID 68569174, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cis-4,5-bis-(3-methylphenyl)imidazolidine-2-thione (30) (2.23 g, 0.00825 mol) and methyl iodide (0.77 mL, 0.0124 mol) in abs. EtOH (30 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 to give 3.24 g of the product 47. 1H NMR (DMSO-d6) δ 10.71 (s, 2 H), 7.10-7.00 (m, 2 H), 7.00-6.90 (m, 2 H), 6.90-6.75 (m, 4 H), 5.73 (s, 2 H), 2.80 (s, 3 H), 2.13 (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-3f8900a5f4494265aaebccd7206614ab
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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