Iodoethane → 2-Ethylsulfanyl-3-(5-fluoro-2-methylphenyl)-3,5-dihydroimidazol-4-one

HRID 1417734Notes

Reaction equation

HRID 1417734 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([NH:8][C:9](=[S:15])[NH:10][CH2:11][C:12](N)=[O:13])[CH:7]=1.[CH2:17](I)[CH3:18]>C(O)C>[CH2:17]([S:15][C:9]1[N:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[CH3:16])[C:12](=[O:13])[CH2:11][N:10]=1)[CH3:18]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 541319612-[3-(5-Fluoro-2-methylphenyl)-thioureido]acetamide

Product 1

HCID 442957712-Ethylsulfanyl-3-(5-fluoro-2-methylphenyl)-3,5-dihydroimidazol-4-oneYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[3-(5-fluoro-2-methylphenyl)-thioureido]-acetamide (6.0 g), ethyl iodide (15.6 g), and ethanol (120 mL) was heated at reflux for 4 hours. The solvent was evaporated. The residue was treated with ethyl acetate (400 mL) and filtered. The filtrate was washed with water (300 mL). The organic phase was evaporated to dryness. The residue was dissolved in ethanol. The solution was saturated with hydrogen chloride. The solvent was evaporated and the residue was crystallized from ethyl acetate and dried under vacuum to give the mono-hydrochloride of the title compound as a white solid (4.2 g), m.p. 181°-183° C. Anal. Calcd. for. C12H13F N2O S . HCl: C, 49.91; H, 4.89; N, 9.70. Found: C, 49.83; H, 4.82; N, 9.71. Mass spectrum (+FAB,[M+H]+) m/z 253. 1H-NMR (DMSO-d6 ; 400 MHz) δ7.50-8.45 (broad s, 2 H), 7.45 (m, 1 H), 7.27-7.34 (m, 2 H), 4.48 (q, 2 H), 3.21 (m, 2 H), 2.10 (s, 3 H), and 1.29 ppm (t, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was evaporated
  4. additionThe residue was treated with ethyl acetate (400 mL)
  5. filtrationfiltered
  6. washThe filtrate was washed with water (300 mL)
  7. customThe organic phase was evaporated to dryness
  8. dissolutionThe residue was dissolved in ethanol
  9. customThe solvent was evaporated
  10. customthe residue was crystallized from ethyl acetate
  11. customdried under vacuum

Sources & evidence

ORD record
ord-ceb1ddc0f281420fb93c1a158969c1a5
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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