Reaktion #62035

Reaktionsgleichung

HCl

KOH

cyanoacetamide

3-phenoxy-phenyl isothiocyanate

→

2-cyano-2-(3-phenoxy-phenylthiocarbamoyl)-acetamide

Ausbeute 72.4%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo a suspension of 85%
2. 2
   Temperaturcooled in a water bath at room temperature
3. 3
   workup.ADDITIONrising to 28° C. during the addition
4. 4
   workup.STIRRINGThe solution was stirred at room temperature for 16 h
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   Sonstigeto remove small amounts of starting material and by-products
7. 7
   SonstigeThe aqueous layer was isolated
8. 8
   FiltrationThe resulting tan precipitate was filtered
9. 9
   Waschenwashed with water
10. 10
    Sonstigedried for 16 hours in a vacuum oven

Vorschrift

To a suspension of 85% powdered KOH in 20 ml DMF was added 1.74 g of cyanoacetamide at room temperature. The solution was stirred at room temperature for 15 minutes and then cooled in a water bath at room temperature. To this solution 4.7 g of 3-phenoxy-phenyl isothiocyanate was added dropwise. The solution exothermed slightly with the internal temperature rising to 28° C. during the addition. The solution was stirred at room temperature for 16 h, then diluted with 150 ml water and extracted with ethyl acetate to remove small amounts of starting material and by-products. The aqueous layer was isolated and acidified with 1N HCl to pH 1 with vigorous stirring. The resulting tan precipitate was filtered, washed with water, and dried for 16 hours in a vacuum oven to afford 4.66 g of 2-cyano-2-(3-phenoxy-phenylthiocarbamoyl)-acetamide.

Quelle