Reaktion #64218

Reaktionsgleichung

isothiocyanate

4-(5-imino-2-thioxo-3,4,4-trimethyl-1-imidazolidinyl)-2-trifluoromethyl-benzonitrile

tetrahydrofuran

→

desired product

4-(4,4-dimethyl-3-(2-hydroxyethyl)-5-imino-2-thioxo-1-imidazolidinyl) 2-trifluoromethyl-benzonitrile

N-(4-cyano-2-trifluoromethyl-phenyl)-2,2-dimethyl-3-oxazolidine carbothioamide

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 30 minutes
2. 2
   Sonstigeevaporated to dryness
3. 3
   SonstigeThe residue was chromatographed on silica
4. 4
   Wascheneluted with a 95-5 methylene chloride-acetone mixture

Vorschrift

A mixture of 1.18 g of the said mixture, 2.11 g of the isothiocyanate of Example 11 and 20 ml of tetrahydrofuran and 0.5 ml of triethylamine was refluxed for 30 minutes and then evaporated to dryness. The residue was chromatographed on silica and eluted with a 95-5 methylene chloride-acetone mixture to obtain 1.26 g of the desired product and 686 mg of N-(4-cyano-2-trifluoromethyl-phenyl)-2,2-dimethyl-3-oxazolidine carbothioamide. The 686 mg were dissolved in 10 ml of ethyl acetate and after the addition of 30 ml of cyclohexane, the mixture was concentrated to 4 ml and vacuum filtered and dried to obtain another 518 mg of product. The raw product was dissolved in 20 ml of isopropanol and the solution was concentrated to 5 ml, vacuum filtered and dried to obtain 1.04 g of the desired product melting at 181° C.

Quelle