반응 #416582

반응 방정식

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

용매

ethyl acetate

methylisobutylketone

반응 조건

후처리

1. 1
   기타To a 50 ml round-bottomed flask equipped with condenser and N2 inlet
2. 2
   기타prepared
3. 3
   온도The reaction was heated
4. 4
   온도at reflux for 5 days
5. 5
   온도cooled
6. 6
   기타evaporated
7. 7
   기타The ethyl acetate layer was separated
8. 8
   세척washed with water and brine
9. 9
   건조dried over sodium sulfate
10. 10
    기타evaporated
11. 11
    기타The residue was chromatographed on silica gel
12. 12
    기타to give a solid
13. 13
    기타precipitated by addition of hydrochloride gas
14. 14
    여과the precipitate filtered
15. 15
    세척washed with ether
16. 16
    기타dried
17. 17
    기타to give a beige solid, 1.536 g (38%), m.p. >300° C. (dec.)

실험 절차

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).

출처