Triethylamine → 4-Imidazolidinone, 1-ethyl-3-(2-phenylethyl)-2-thioxo-

HRID 1957322Notes

Reaction equation

HRID 1957322 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[CH2:8]([N:16]=[C:17]=[S:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:3]1[CH2:4][C:5](=[O:7])[N:16]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:17]1=[S:18])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16741Phenethyl IsothiocyanateHCID 316542N-Ethylglycine

Product 1

HCID 114024004-Imidazolidinone, 1-ethyl-3-(2-phenylethyl)-2-thioxo-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of the crude N-ethyl glycine (18.4 g), phenethyl-isothiocyanate (16.3 g), triethyl amine (20.2 g) and chloroform (300 mL) was heated at reflux for 18 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and water (300 mL). The organic phase was washed with 1N HCl (2×300 mL), then evaporated to dryness. Purification was achieved by flash chromatography on silica gel (20% ethyl acetate in hexane) The title compound (15.0 g) was obtained as an off-white solid, m.p. 66°-68° C. Anal. Calcd. for. C13H16N2 O S: C, 62.87; H, 6.49; N, 11.28. Found: C, 63.03; H, 6.49; N, 11.32. Mass spectrum (EI, M.+) m/z 248.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (400 mL)
  5. washThe organic phase was washed with 1N HCl (2×300 mL)
  6. customevaporated to dryness
  7. customPurification
  8. customwas obtained as an off-white solid, m.p. 66°-68° C

Sources & evidence

ORD record
ord-b60ffb25a46d4e94855da4f1b7ffdb70
Source dataset
uspto-grants-1998_07
Patent number
US05783707

Reaction notes

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