N-Phenylglycine ethyl ester → 3-(3-Chloro-2-methylphenyl)-1-phenyl-2-thioxo-imidazolidin-4-one

HRID 742266

Reaktionsgleichung

Reaktionsgleichung von HRID 742266
C(O[C:4](=[O:13])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[Cl:14][C:15]1[C:16]([CH3:24])=[C:17]([N:21]=[C:22]=[S:23])[CH:18]=[CH:19][CH:20]=1>C(Cl)(Cl)Cl>[Cl:14][C:15]1[C:16]([CH3:24])=[C:17]([N:21]2[C:4](=[O:13])[CH2:5][N:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:22]2=[S:23])[CH:18]=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 75190N-Phenylglycine ethyl esterHCID 1405041-Chloro-3-isothiocyanato-2-methylbenzene

Produkt 1

HCID 189682163-(3-Chloro-2-methylphenyl)-1-phenyl-2-thioxo-imidazolidin-4-oneAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of N-phenyl glycine ethyl ester (8.95 g), 3-chloro-2-methylphenylisothiocyanate (9.18 g), and chloroform (200 mL) was heated at reflux for 18 hours. The solvent was evaporated to dryness. The residue was mixed with ethanol (150 mL), and triethyl amine (3 mL). The mixture was heated at reflux for 3 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (300 mL) and washed with 1N HCl (2×200 mL), then with water (200 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was treated with diethyl ether. The solid was collected by filtration and air dried to give the title compound (5.3 g) as an off-white solid, m.p. 154°-156° C. Anal. Calcd. for. C16H13Cl N2O S: C, 60.66; H, 4.14; N, 8.84. Found: C, 60.48; H, 4.05; N, 8.76. Mass spectrum (+FAB, [M+H]+) m/z 317/319.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated to dryness
  4. additionThe residue was mixed with ethanol (150 mL), and triethyl amine (3 mL)
  5. temperatureThe mixture was heated
  6. temperatureat reflux for 3 hours
  7. customThe solvent was evaporated
  8. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  9. washwashed with 1N HCl (2×200 mL)
  10. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  11. customevaporated to dryness
  12. additionThe residue was treated with diethyl ether
  13. filtrationThe solid was collected by filtration and air
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-094b8222c69d4b80aee177bd9ba4b72e
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554607

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