Iodoethane → 3-(2,6-Dimethylphenyl)-2-ethylsulfanyl-3,5-dihydro-imidazol-4-one

HRID 1417741Notes

Reaction equation

HRID 1417741 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[S:16])[NH:11][CH2:12][C:13](N)=[O:14].[CH2:17](I)[CH3:18]>C(O)C>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N:9]1[C:13](=[O:14])[CH2:12][N:11]=[C:10]1[S:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 539479742-[3-(2,6-Dimethylphenyl)-thioureido]-acetamide

Product 1

HCID 442955033-(2,6-Dimethylphenyl)-2-ethylsulfanyl-3,5-dihydro-imidazol-4-oneYield 28.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by the procedure described in Example 12 using 8.0 g of 2-[3-(2,6-dimethylphenyl)-thioureido]-acetamide, 25.0 g of ethyl iodide, and (200 mL) ethanol. Crystallization from hexane/diethyl ether mixture afforded the title compound as a light yellow solid (2.4 g), m.p. 86°-88° C. Anal. Calcd. for. C12H16N2O S: C, 62.87; H, 6.49; N, 11.28. Found: C, 62.98; H, 6.57; N, 11.30. Mass spectrum (El, M.+) m/z 248. 1H-NMR (DMS-d6 ; 400 MHz) δ7.27-7.30 (m, 1 H), 7.21 (m, 1 H), 7.19 (m, 1 H), 7.33 (d, 1 H), 4.42 (s, 2 H), 3.06 (q, 2 H), 2.07 (s, 6H), and 1.26 ppm (t, 3 H).

Workup

  1. customThe title compound was prepared by the procedure
  2. customCrystallization from hexane/diethyl ether mixture

Sources & evidence

ORD record
ord-f42863fb631c4d5ab23009e004deeb24
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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