Triethylamine → 3-(5-Chloro-2-methylphenyl)-1-methyl-2-thioxo-imidazolidin-4-one

HRID 742224

Reaktionsgleichung

Reaktionsgleichung von HRID 742224
Cl.C(O[C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:20])=[C:15]([N:17]=[C:18]=[S:19])[CH:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:20])=[C:15]([N:17]2[C:5](=[O:9])[CH2:6][N:7]([CH3:8])[C:18]2=[S:19])[CH:16]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 171173Ethyl N-methylaminoacetate hydrochloride

Produkt 1

HCID 189682093-(5-Chloro-2-methylphenyl)-1-methyl-2-thioxo-imidazolidin-4-oneAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of sarcosine ethyl ester hydrochloride (7.68 g), 5-chloro-2-methylphenyl-isothiocyanate (9.18 g), triethyl amine (12 g) and chloroform (200 mL) was heated at reflux for 5 hours. The mixture was cooled to ambient temperature, washed with 1N HCl (2×200 mL), then with water (200 mL) The organic phase was evaporated to dryness. The residue was crystallized from ethanol to give the title compound (9.2 g) as a tan solid, m.p. 132°-134° C. Anal. Calcd. for C11H11Cl N2O S: C, 51.87; H, 4.35; N, 11.00. Found: C, 51.79; H, 4.12; N, 10.73. Mass spectrum (El, M.+) m/z 254/256.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. washwashed with 1N HCl (2×200 mL)
  4. customwith water (200 mL) The organic phase was evaporated to dryness
  5. customThe residue was crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-aa20aad8e73d45e7bf7f247eee9b20b7
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554607

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