Triethylamine → 3-(5-Chloro-2-methylphenyl)-1-isopropyl-2-thioxo-imidazolidin-4-one

HRID 399604

Reaction equation

HRID 399604 reaction equation
[CH:1]([NH:4][CH2:5][C:6]([OH:8])=O)([CH3:3])[CH3:2].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:19])=[C:14]([N:16]=[C:17]=[S:18])[CH:15]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:19])=[C:14]([N:16]2[C:6](=[O:8])[CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[C:17]2=[S:18])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 414244NoName_76

Product 1

HCID 189682133-(5-Chloro-2-methylphenyl)-1-isopropyl-2-thioxo-imidazolidin-4-oneYield 54.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of the crude N-isopropyl glycine (21.2 g), 5-chloro-2-methylphenyl-isothiocyanate (18.3 g), triethyl amine (21.0 g) and chloroform (300 mL) was heated at reflux for 4 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and water (300 mL). The organic phase was washed with 2N HCl (2×300 mL), then with water. The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. Crystallization from ethanol afforded the title compound (15.4 g) as a peach solid, m.p. 142°-144° C. Anal. Calcd. for. C13H15Cl N2O S: C, 55.21; H, 5.35; N, 9.91. Found: C, 55.07; H, 5.20; N, 9.82. Mass spectrum (+FAB, [M+H]+) m/z 283/285.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (400 mL)
  5. washThe organic phase was washed with 2N HCl (2×300 mL)
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customCrystallization from ethanol

Sources & evidence

ORD record
ord-a3a49c614e55447b8d91db8a18e607db
Source dataset
uspto-grants-1998_10
Patent number
US05821372

Linked notes

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