Methyl iodide → HCID 68569003, compound

HRID 18713Notes

Reaction equation

HRID 18713 reaction equation
[F: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[F:19])[NH:11][C:10](=[S:20])[NH:9]1.[CH3:21][I:22]>CCO>[IH:22].[F: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[F:1])[NH:9][C:10]([S:20][CH3:21])=[N:11]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86596311cis-4,5-bis-(2-Fluorophenyl)imidazolidine-2-thione

Product 1

HCID 68569003HCID 68569003, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of cis-4,5-bis-(2-fluorophenyl)imidazolidine-2-thione (26) (2.45 g, 0.0084 mol) and methyl iodide (0.79 mL, 0.012 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 crystallized from abs EtOH/Et2O to give 3.42 g of the product 43. 1H NMR (DMSO-d6) δ 10.85 (s, 2 H), 7.30-7.10 (m, 4 H), 7.10-6.90 (m, 4 H), 6.04 (s, 2 H), 2.80 (s, 3 H); MS: m/z 305 (M++1).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue crystallized from abs EtOH/Et2O

Sources & evidence

ORD record
ord-793abe426adc47dda9ee3dbc43ce1ae3
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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