Reaktion #416582

Reaktionsgleichung

sodium carbonate

sodium iodide

4-(4-(2-chloroethyl)phenyl)-2-aminothiazole hydrobromide

N-(3-benzisothiazolyl) piperazine

diisopropylethylamine

→

4-(4-(2-(4 -(3-Benzisothiazolyl)piperazinyl)ethyl)phenyl)-2-aminothiazole

Lösungsmittel

ethyl acetate

methylisobutylketone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 50 ml round-bottomed flask equipped with condenser and N2 inlet
2. 2
   Sonstigeprepared
3. 3
   TemperaturThe reaction was heated
4. 4
   Temperaturat reflux for 5 days
5. 5
   Temperaturcooled
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe ethyl acetate layer was separated
8. 8
   Waschenwashed with water and brine
9. 9
   Trocknendried over sodium sulfate
10. 10
    Sonstigeevaporated
11. 11
    SonstigeThe residue was chromatographed on silica gel
12. 12
    Sonstigeto give a solid
13. 13
    Sonstigeprecipitated by addition of hydrochloride gas
14. 14
    Filtrationthe precipitate filtered
15. 15
    Waschenwashed with ether
16. 16
    Sonstigedried
17. 17
    Sonstigeto give a beige solid, 1.536 g (38%), m.p. >300° C. (dec.)

Vorschrift

To a 50 ml round-bottomed flask equipped with condenser and N2 inlet were added 2.4 g (7.53 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-aminothiazole hydrobromide, 1.65 g (7.53 mmol) of N-(3-benzisothiazolyl) piperazine (prepared according to the method of U.S. Pat. No. 4,411,901), 1.3 ml (7.53 mmol) of diisopropylethylamine, 1.6 g (15.1 mmol) of sodium carbonate, 2 mg of sodium iodide, and 25 ml of methylisobutylketone. The reaction was heated at reflux for 5 days, cooled, evaporated, and taken up in ethyl acetate/water. The ethyl acetate layer was separated, washed with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using ethyl acetate as eluent to give a solid. The solid was taken up in hot ethyl acetate, precipitated by addition of hydrochloride gas, the precipitate filtered, washed with ether, and dried to give a beige solid, 1.536 g (38%), m.p. >300° C. (dec.). NMR (DMSO-d6): 3.2-3.8 (m, 10H), 4.1 (m, 2H), 7.25 (s, 1H), 7.4-8.2 (m, 8H), 11.5 (bs, 2H).

Quelle