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

HRID 1417730Notes

Reaction equation

HRID 1417730 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-one

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 mono-hydrochloride 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, 2 H), 7.51 (m, 1 H), 7.44 (t, 1 H), 7.39 (m, 1 H), 4.51 (q, 2 H), 3.12 (q, 2 H), 2.17 (s, 3 H), and 1.27 ppm (t, 3 H).

Workup

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

Sources & evidence

ORD record
ord-08c68caee35145ceb4913bfa61450027
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

Loading…