Methyl iodide → HCID 68569331, compound

HRID 18716Notes

Reaction equation

HRID 18716 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[NH:11][C:10](=[S:20])[NH:9]1.[CH3:21][I:22]>CCO>[IH:22].[CH3:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C@H:12]1[C@@H:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[NH:9][C:10]([S:20][CH3:21])=[N:11]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86596314cis-4,5-bis-(2-Methylphenyl)imidazolidine-2-thione

Product 1

HCID 68569331HCID 68569331, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cis-4,5-bis-(2-methylphenyl)imidazolidine-2-thione (29) (6.08 g, 0.0215 mol) and methyl iodide (2.01 mL, 0.0323 mol) in abs. EtOH (50 mL) is heated at 85° 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 8.79 g of the product 46. 1H NMR (DMSO-d6) δ 10.67 (s, 2 H), 7.10-6.90 (m, 8 H), 6.02 (s, 2 H), 2.79 (s, 3 H), 2.16 (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-52145258886840f2bd329d8b0a59598b
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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