Iodoethane → HCID 9795388, compound

HRID 1449598Notes

Reaction equation

HRID 1449598 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([NH:8][C:9](=[S:15])[NH:10][CH2:11][C:12](N)=[O:13])[CH:7]=1.[CH2:17](I)[CH3:18]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([N:8]2[C:12](=[O:13])[CH2:11][N:10]=[C:9]2[S:15][CH2:17][CH3:18])[CH:7]=1

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 53995114HCID 53995114, compound

Product 1

HCID 9795388HCID 9795388, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[3-(5-chloro-2-methylphenyl)-thioureido]-acetamide (25.8 g) and ethyl iodide (32.0 g) was heated at reflux in ethanol (500 mL) for 5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (500 mL) and water (300 mL). The organic phase was washed with water, dried over anhydrous MgSO4, then evaporated to dryness. The residue was triturated with diethyl ether and the solid was collected by filtration and dried to give the title compound (17.0 g) as a yellow solid, m.p. 137°-139° C. Anal. Calcd. for. C12H13Cl N2O S: C, 53.63; H, 4.88; N, 10.42. Found: C, 53.58; H, 4.74; N, 10.32. Mass spectrum (EI, M.+) m/z 268/270. 1H-NMR (DMSO-d6 ; 400 MHz) δ7.45-7.49 (m, 1H), 7.40-7.43 (m, 2H), 4.35 (dd, 2H), 3.07 (m, 2H), 2.1 (s, 3H), and 1.28 ppm (t, 3H).

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated to dryness
  7. customThe residue was triturated with diethyl ether
  8. filtrationthe solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-42defc09e5b145509de93de775f34a40
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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