Iodoethane → 3-(5-Chloro-2-methoxyphenyl)-2-ethylsulfanyl-3,5-dihydro-imidazol-4-one

HRID 1449600Notes

Reaction equation

HRID 1449600 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([NH:8][C:9](=[S:15])[NH:10][CH2:11][C:12](N)=[O:13])[CH:7]=1.[CH2:18](I)[CH3:19]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([N:8]2[C:12](=[O:13])[CH2:11][N:10]=[C:9]2[S:15][CH2:18][CH3:19])[CH:7]=1

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 537435902-[3-(5-Chloro-2-methoxyphenyl)-thioureido]acetamide

Product 1

HCID 442958233-(5-Chloro-2-methoxyphenyl)-2-ethylsulfanyl-3,5-dihydro-imidazol-4-oneYield 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[3-(5-chloro-2-methoxyphenyl)-thioureido]-acetamide (11.0 g) and ethyl iodide (12.5 g) in ethanol (400 mL) was heated at reflux for 4.5 hours. The solvent was evaporated. The residue was dissolved in chloroform (500 mL) and washed with water. The organic phase was dried over anhydrous MgSO4, then evaporated to dryness. The residue was crystallized from ethanol to give the title compound (6.1 g) as a tan solid, m.p. 113°-115° C. Anal. Calcd. for. C12H13Cl N2O2S: C, 50.61; H, 4.60; N,9.84. Found: C, 50.32; H, 4.59; N, 9.77. Mass spectrum (ESI+, [M+H]+) m/z 285/287. 1H-NMR (DMSO-d6; 400 MHz) 15 7.53 (m, 1H), 7.41 (d, 1H), 7.22 (d, 1H), 4.31 (dd, 2H), 3.77 (s, 3H), 3.05 (m, 2H), and 1.26 ppm (t, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in chloroform (500 mL)
  5. washwashed with water
  6. dry with materialThe organic phase was dried over anhydrous MgSO4
  7. customevaporated to dryness
  8. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-6b5ad417cc264c1bb756d0e022143562
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

Loading…