Reaktion #1747350

Reaktionsgleichung

dichloromethane

NaOH

5-cyano-1-(2,6-dimethylphenyl)uracil

1,1,2,2-tetrachloroethanesulphenyl chloride

→

5-cyano-1-(2,6-dimethylphenyl)-3-(1,1,2,2-tetrachloroethanesulphenyl)uracil

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeobtained as in Example 1
2. 2
   workup.ADDITIONis added
3. 3
   Sonstigeprepared by the method of U.S
4. 4
   SonstigeThe aqueous layer is separated
5. 5
   TrocknenThe dichloromethane solution is dried
6. 6
   SonstigeThe unreacted sulphenyl chloride is then removed by trituration with pentane/dichloromethane (4:1)
7. 7
   SonstigeThe resultant crude product is purified
8. 8
   Sonstigeby slurrying at 30° in 60 ml of ethanol-free chloroform
9. 9
   Filtrationfiltered
10. 10
    workup.ADDITIONTo the filtrate is added hexane to the cloud point
11. 11
    Filtrationthe mixture is then filtered

Vorschrift

To an ice cold solution of 1.60 g (0.04 mol) of NaOH in 45 ml of water is added 9.64 g (0.04 mol) of 5-cyano-1-(2,6-dimethylphenyl)uracil, obtained as in Example 1. After dissolution, 50 ml of ice cold dichloromethane is added, followed by a solution of 9.36 g (0.04 mol) of 1,1,2,2-tetrachloroethanesulphenyl chloride (prepared by the method of U.S. Pat. No. 3,395,180) in 15 ml. of dichloromethane. The mixture is stirred for 30 min at 4°. The aqueous layer is separated and discarded. The dichloromethane solution is dried and stripped at aspirator pressure. The unreacted sulphenyl chloride is then removed by trituration with pentane/dichloromethane (4:1). The resultant crude product is purified by slurrying at 30° in 60 ml of ethanol-free chloroform, allowed to cool to RT and filtered. To the filtrate is added hexane to the cloud point, and the mixture is then filtered to yield 5-cyano-1-(2,6-dimethylphenyl)-3-(1,1,2,2-tetrachloroethanesulphenyl)uracil, m.p. 180°-183°.

Quelle