Iodoethane → HCID 12031585, compound

HRID 1449609Notes

Reaction equation

HRID 1449609 reaction equation
[C:1]1([NH:7][C:8](=[S:14])[NH:9][CH2:10][C:11](N)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15](I)[CH3:16]>C(O)C>[CH2:15]([S:14][C:8]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11](=[O:12])[CH2:10][N:9]=1)[CH3:16]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 53927476HCID 53927476, compound

Product 1

HCID 12031585HCID 12031585, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(3-phenyl-thioureido)-acetamide (7.1 g), ethyl iodide (18.0 g), and ethanol (300 mL) was heated at reflux for 2 hours. The solvent was evaporated. The residue was dissolved in chloroform (300 mL) and water (300 mL). The organic phase was washed with water, dried over anhydrous MgSO4, then evaporated to dryness. The residue was crystallized from ethyl acetate/hexane to give the title compound (3.1 g), m.p. 79°-81° C. Anal. Calcd. for. C11H12N2O S: C, 59.97; H, 5.49; N, 12.72. Found: C, 59.67; H, 5.35; N, 12.70. Mass spectrum (El, M.+) m/z 220. 1H-NMR (DMSO-d6 ; 400 MHz) δ7.43-7.52 (m, 3H), 7.28-7.31 (m, 2H), 4.32 (s, 2H), 3.07 (q, 2H), and 1.27 ppm (t, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in chloroform (300 mL)
  5. washThe organic phase was washed with water
  6. dry with materialdried over anhydrous MgSO4
  7. customevaporated to dryness
  8. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-640c7afb42a24b45938fb963f885a961
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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