Iodoethane → 3-(2-Chloro-6-methylphenyl)-2-ethylsulfanyl-3,5-dihydroimidazol-4-one

HRID 1449607Notes

Reaction equation

HRID 1449607 reaction equation
[Cl: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]>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[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 543940602-[3-(2-Chloro-6-methylphenyl)-thioureido]-acetamide

Product 1

HCID 442958223-(2-Chloro-6-methylphenyl)-2-ethylsulfanyl-3,5-dihydroimidazol-4-oneYield 36.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The title compound was prepared by the procedure described in Example 6 using 12.9 g of 2-[3-(2-chloro-6-methylphenyl)-thioureido]-acetamide, and 18.0 g of ethyl iodide. The hydrochloride salt was prepared in ethereal hydrogen chloride. Crystallization from ethyl acetate afforded the title compound as the monohydrochloride as a light yellow solid (4.9 g), m.p. 152°-154° C. (dec.). Anal. Calcd. for. C12H13Cl N2O S. HCl: C, 47.22; H, 4.62; N, 9.18. Found: C, 46.99; H, 4.60; N, 9.16. Mass spectrum (+FAB, [M+H]+) m/z 269/271 1H-NMR (DMSO-d6 ; 400 MHz) δ8.28 (broad s, 2H), 7.51 (m, 1H), 7.44 (t, 1H), 7.39 (m, 1H), 4.51 (q, 2H), 3.12 (q, 2H), 2.17 (s, 3H), and 1.27 ppm (t, 3H).

Workup

  1. customThe title compound was prepared by the procedure
  2. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2e1bc665b30c43c794f116b1abffcea3
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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