Triethylamine → 4-Imidazolidinone, 3-(5-chloro-2-methylphenyl)-1-ethyl-2-thioxo-

HRID 742238Notes

Reaction equation

HRID 742238 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:18])=[C:13]([N:15]=[C:16]=[S:17])[CH:14]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:18])=[C:13]([N:15]2[C:5](=[O:7])[CH2:4][N:3]([CH2:1][CH3:2])[C:16]2=[S:17])[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 316542N-Ethylglycine

Product 1

HCID 98382824-Imidazolidinone, 3-(5-chloro-2-methylphenyl)-1-ethyl-2-thioxo-Yield 56.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of the crude N-ethyl glycine (9.23 g), 5-chloro-2-methylphenylisothiocyanate (9.18 g), triethyl amine (10 g) and chloroform (250 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 through crystallization from ethanol. The title compound (7.6 g) was obtained as a light pink solid, m.p. 152°-154° C. Anal. Calcd. for. C12H13Cl N2O S: C, 53.63; H, 4.88; N, 10.42. Found: C, 53.36; H, 4.79; N, 10.35. Mass spectrum (EI, M.+) m/z 268/270.

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 achieved through crystallization from ethanol

Sources & evidence

ORD record
ord-ad88353a86ad486c896882e297e90615
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Reaction notes

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