Iodoethane → HCID 44295501, compound

HRID 1417738Notes

Reaction equation

HRID 1417738 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[S:16])[NH:11][CH2:12][C:13](N)=[O:14])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH2:17](I)[CH3:18]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[CH2:12][N:11]=[C:10]2[S:16][CH2:17][CH3:18])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 54019612HCID 54019612, compound

Product 1

HCID 44295501HCID 44295501, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[3-(3-chloro-4-methylphenyl)-thioureido]-acetamide (10.0 g), ethyl iodide (17.5 g), and ethanol (200 mL) was heated at reflux for 2.5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (500 mL) and water (500 mL). The organic phase was washed with water (2×300 mL). The organic phase was 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 Na2SO4 then evaporated to dryness. The residue was stirred in diethyl ether and filtered to give the title compound (8.4 g) as a white solid, m.p. 133°-135° C. Anal. Calcd. for. C12H13Cl N2O S: C, 53.63; H, 4.88; N,10.42. Found: C, 53.66; H, 4.78; N, 10.39. Mass spectrum (EI, M.+) m/z 268/270. 1H-NMR (DMSO-d6 ; 400 MHz) δ7.47 (d, 1 H), 7.43 (d, 1 H), 7.20 (dd, 1 H), 4.29 (s, 2 H), 3.07 (q, 2 H), 2.36 (s, 3 H), and 1.28 ppm (t, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  5. washThe organic phase was washed with water (2×300 mL)
  6. extractionThe organic phase was 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 Na2SO4
  11. customthen evaporated to dryness
  12. filtrationfiltered

Sources & evidence

ORD record
ord-d6bc7b76e064486abb79e6803db0ec21
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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