Triethylamine → 1-Ethyl-3-(2-ethyl-6-isopropylphenyl)-2-thioxo-imidazolin-4-one

HRID 343603

Reaction equation

HRID 343603 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[CH2:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([CH3:18])[CH3:17])[C:11]=1[N:19]=[C:20]=[S:21])[CH3:9].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:3]1[CH2:4][C:5](=[O:7])[N:19]([C:11]2[C:12]([CH:16]([CH3:17])[CH3:18])=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:8][CH3:9])[C:20]1=[S:21])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1442342-Ethyl-6-isopropylphenyl isothiocyanateHCID 316542N-Ethylglycine

Product 1

HCID 111853871-Ethyl-3-(2-ethyl-6-isopropylphenyl)-2-thioxo-imidazolin-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of the crude N-ethyl glycine (18.4 g), 2-ethyl-6-isopropylphenyl-isothiocyanate, (20.5 g), triethyl amine (20.2 g) and chloroform (300 mL) was heated at reflux for 6 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (500 mL) and washed with water (500 mL). The organic phase was evaporated to dryness. The residue was dissolved in ethanol (50 mL), then diluted with diethyl ether (200 mL). The solution was saturated with hydrogen chloride. The mixture was filtered. The solid was discarded. The filtrate was evaporated to dryness. Purification was achieved by flash chromatography on silica gel (5-10% ethyl acetate in hexane). Crystallization from diethyl ether/hexane afforded pure title compound (7.5 g) as a white solid, m.p. 77°-79° C. Anal. Calcd. for. C16H22N2OS: C, 66.17; H, 7.64; N, 9.65. Found: C, 66.12; H, 7.77; N, 9.69. Mass spectrum (EI, M.+) m/z 290.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  5. washwashed with water (500 mL)
  6. customThe organic phase was evaporated to dryness
  7. dissolutionThe residue was dissolved in ethanol (50 mL)
  8. additiondiluted with diethyl ether (200 mL)
  9. filtrationThe mixture was filtered
  10. customThe filtrate was evaporated to dryness
  11. customPurification
  12. customCrystallization from diethyl ether/hexane afforded pure title compound (7.5 g) as a white solid, m.p. 77°-79° C

Sources & evidence

ORD record
ord-1d5a56b47b9343c49c3780fb7af10a54
Source dataset
uspto-grants-1999_01
Patent number
US05861517

Linked notes

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