Triethylamine → 1-Allyl-3-(5-chloro-2-methylphenyl)-2-thioxo-imidazolidin-4-one

HRID 742281

Reaktionsgleichung

Reaktionsgleichung von HRID 742281
[CH2:1]([NH:4][CH2:5][C:6]([OH:8])=O)[CH:2]=[CH2:3].[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>[CH2:1]([N:4]1[CH2:5][C:6](=[O:8])[N:16]([C:14]2[CH:15]=[C:10]([Cl:9])[CH:11]=[CH:12][C:13]=2[CH3:19])[C:17]1=[S:18])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 76651N-Allylglycine

Produkt 1

HCID 189682071-Allyl-3-(5-chloro-2-methylphenyl)-2-thioxo-imidazolidin-4-oneAusbeute 15,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of N-allyl glycine (17.4 g), 5-chloro-2-methylphenyl-isothiocyanate (20.1 g), triethylamine (20.2 g), and methylene chloride (150 mL) was heated at reflux for 2 hours. The reaction mixture was evaporated to dryness. Purification was achieved by flash chromatography on silica gel (methylene chloride). Recrystallization from Hexane-EtOAc afford the title compound (4.8 g) as yellow solid, m.p. 106°-109° C. Anal. Calcd. for. C13H13N2O Cl S: C, 55.61; H, 4.67; N, 9.98. Found: C, 55.45; H, 4.56; N, 9.72. Mass spectrum (EI, M.+) m/z 280.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe reaction mixture was evaporated to dryness
  4. customPurification
  5. customRecrystallization from Hexane-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-22962308ac7b464db58942830d83c9a0
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554607

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