Triethylamine → 1-Ethyl-3-(5-fluoro-2-methylphenyl)-2-thioxo-imidazolidin-4-one

HRID 399600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399600
[CH2:1]([NH:3][CH2:4][C:5]([OH:7])=O)[CH3:2].[F: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>[CH2:1]([N:3]1[CH2:4][C:5](=[O:7])[N:15]([C:13]2[CH:14]=[C:9]([F:8])[CH:10]=[CH:11][C:12]=2[CH3:18])[C:16]1=[S:17])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 316542N-EthylglycineHCID 5194435-Fluoro-o-tolyl Isothiocyanate

Produkt 1

HCID 114252721-Ethyl-3-(5-fluoro-2-methylphenyl)-2-thioxo-imidazolidin-4-oneAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of the crude N-ethyl glycine (11.5 g), 5-fluoro-2-methylphenyl-isothiocyanate (10.42 g), triethyl amine (12.5 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. The residue was dissolved in diethyl ether (300 mL) and washed with water (200 mL). The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness. Crystallization from ethanol afforded the title compound (6.5 g) as a pink solid, m.p. 98°-100° C. Anal. Calcd. for. C12H13F N2O S: C, 57.13; H, 5.19; N, 11.10. Found: C, 56.88; H, 5.17; N, 11.05. Mass spectrum (EI, M.+) m/z 252.

Aufarbeitung

  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. dissolutionThe residue was dissolved in diethyl ether (300 mL)
  12. washwashed with water (200 mL)
  13. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  14. customevaporated to dryness
  15. customCrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-da9371abb57648ee9feeddba89c2fa36
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821372

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