Chlorosuccinimide → 5-Chloro-3-cyano-2-(1,1-dipropoxymethylenamino)thiophene
Reaktionsgleichung
[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[N:8]=[C:9]([O:14][CH2:15][CH2:16][CH3:17])[O:10][CH2:11][CH2:12][CH3:13])#[N:2].[Cl:18]N1C(=O)CCC1=O>N1C=CC=CC=1>[Cl:18][C:6]1[S:5][C:4]([N:8]=[C:9]([O:14][CH2:15][CH2:16][CH3:17])[O:10][CH2:11][CH2:12][CH3:13])=[C:3]([C:1]#[N:2])[CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
In a sulfonation flask, 3.02 g (0.012 mol) 3-cyano-2-(1,1-dipropoxymethylenamino)thiophene, are added, with stirring to 15 ml of absolute pyridine. The internal temperature is then raised to 60° C. and 1.9 g (0.0144 mol) N-chlorosuccinimide are added in three portions. After stirring for 3 hours at 60° C., the pyridine is removed in a water jet vacuum and the residue taken up in ethylacetate. The organic phase is washed twice with water and after drying, the solvent is removed in a water jet vacuum. The crude product is purified by column chromatography over silica gel (eluant: tert.butylmethylether/hexane 1:6). Yield: 3.5 g of 5-chloro-3-cyano-2-(1,1-dipropoxymethyleneamino)thiophene in the form of brownish crystals, m.p. 55-57° C.