Triethylamine → 3-(2,6-Diisopropylphenyl)-1-ethyl-2-thioxo-imidazolidin-4-one

HRID 343602

Reaction equation

HRID 343602 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[C:12]=1[N:20]=[C:21]=[S:22])([CH3:10])[CH3:9].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:18])[CH3:19])[C:12]=1[N:20]1[C:5](=[O:7])[CH2:4][N:3]([CH2:1][CH3:2])[C:21]1=[S:22])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1411942-Isothiocyanato-1,3-bis(propan-2-yl)benzeneHCID 316542N-Ethylglycine

Product 1

HCID 153894883-(2,6-Diisopropylphenyl)-1-ethyl-2-thioxo-imidazolidin-4-oneYield 27%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of the crude N-ethyl glycine (18.4 g), 2,6-diisopropylphenyl-isothiocyanate (21.9 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 through crystallization from ethanol. The title compound (8.2 g) was obtained as a light yellow solid, m.p. 159°-161° C. Anal. Calcd. for. C17H24N2OS: C, 67.07; H, 7.94; N, 9.20. Found: C, 66.92; H, 8.03; N, 9.13. Mass spectrum (PBEI, M.+) m/z 304.

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-8e0fe235b4ed40b4968bb1d19c7ebcf2
Source dataset
uspto-grants-1999_01
Patent number
US05861517

Linked notes

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