Iodoethane → HCID 44295836, compound

HRID 1449604Notes

Reaction equation

HRID 1449604 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[S:15])[NH:10][CH2:11][C:12](N)=[O:13].[CH2:16](I)[CH3:17]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[CH2:11][N:10]=[C:9]1[S:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 54543212HCID 54543212, compound

Product 1

HCID 44295836HCID 44295836, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[3-(2-chlorophenyl)-thioureido]-acetamide (12.2 g), ethyl iodide (15.6 g), and ethanol (200 mL) was heated at reflux for 5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and water (300 mL). The organic phase was washed with water (2×300 mL). The organic phase was then extracted with 2N HCl (2×500 mL). The acid extract was neutralized with solid sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous MgSO4 then evaporated to dryness. The residue was dissolved in ethanol and the solution was saturated with hydrogen chloride. The solvent was evaporated and the residue was crystallized from ethyl acetate to give the hydrochloride salt of the title compound (8.4 g) as an off-white solid, m.p. 149°-150° C. (dec.). Anal. Calcd. for. C11H11Cl N2O S. HCl: C, 45.37; H, 4.15; N, 9.62. Found: C, 44.97; H, 4.06; N, 9.51. Mass spectrum (EI, M.+) m/z 254/256. 1H-NMR (DMSO-d6 ; 400 MHz) δ7.69 (m, 1H), 7.50-7.58 (m, 3H), 4.45 (q, 2H), 3.11-3.17 (m, 2H), and 1.27 ppm (t, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (400 mL)
  5. washThe organic phase was washed with water (2×300 mL)
  6. extractionThe organic phase was then extracted with 2N HCl (2×500 mL)
  7. extractionThe acid extract
  8. extractionextracted with ethyl acetate
  9. washThe organic phase was washed with water
  10. dry with materialdried over anhydrous MgSO4
  11. customthen evaporated to dryness
  12. dissolutionThe residue was dissolved in ethanol
  13. customThe solvent was evaporated
  14. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a242b2f4e65a4f38906c50e428d6ab3b
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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