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

HRID 1449617Notes

Reaction equation

HRID 1449617 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[S:15])[NH:10][CH2:11][C:12](N)=[O:13])=[C:4]([CH3:16])[CH:3]=1.[CH2:17](I)[CH3:18]>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][N:10]=[C:9]2[S:15][CH2:17][CH3:18])=[C:4]([CH3:16])[CH:3]=1

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 536560542-[3-(4-Chloro-2-methylphenyl)-thioureido]-acetamide

Product 1

HCID 442957763-(4-Chloro-2-methylphenyl)-2-ethylsulfanyl-3,5-dihydroimidazol-4-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The title compound was prepared by the procedure described in Example 6 using 18.0 g of 2-[3-(4-chloro-2-methylphenyl)-thioureido]-acetamide, and 25.0 g of ethyl iodide. The hydrochloride salt was prepared in ethereal hydrogen chloride. Crystallization from ethyl acetate afforded the title compound as an off-white solid, mono-hydrochloride (17.6 g), m.p. 166°-168° C. (dec.). Anal. Calcd. for. C12H13Cl N2O S. HCl: C, 47.22; H, 4.62; N, 9.18. Found: C, 47.24; H, 4.45; N, 9.05. Mass spectrum (+FAB, [M+H]+) m/z 269/271 1H-NMR (DMSO-d6 ; 400 MHz) δ9.05-9.78 (broad s, 2H), 7.53 (m, 1H), 7.44 (d, 1H), 7.41 (d, 1H), 7.33 (d, 1H), 4.48 (q, 2H), 3.20 (m, 2H), 2.13 (s, 3H), and 1.29 ppm (t, 3H).

Workup

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

Sources & evidence

ORD record
ord-dee286f8ab7a46edb2696eacc69ad520
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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