반응 #9342

반응 방정식

diisobutylamine

Diisobutylamine

6-hydroxy-7-propyl-3-trifluoromethylbenzisoxazole

sodium bisulfite

benzisoxazole

sulfuryl chloride

→

title compound

5-Chloro-6-hydroxy-7-propyl-3-trifluoromethyl-1,2-benzisoxazole

용매

toluene

ethyl ether

반응 조건

후처리

1. 1
   기타results in a suspension which
2. 2
   기타The phases were separated
3. 3
   세척The ether phase was washed with brine
4. 4
   건조dried over Na2SO4
5. 5
   기타The solvent was evaporated in vac
6. 6
   기타to give an orange solid which
7. 7
   기타was purified by chromatography on silica gel eluting with acetone:hexane (2:98)

실험 절차

Diisobutylamine (0.8 ml, 0.10 eq) and 6-hydroxy-7-propyl-3-trifluoromethylbenzisoxazole (11 gm, 1.0 eq) were dissolved in toluene (275 ml) at room temperature. Slow addition of sulfuryl chloride (4.20 ml, 1.15 eq) results in a suspension which was stirred overnight. Additional diisobutylamine (total 1.6 ml, 0.4 eq) was added in four equal portions over 24 hr until no further starting benzisoxazole was detected by analytical TLC. The reaction mixture was poured into saturated sodium bisulfite (500 ml) and ethyl ether (700 ml). The phases were separated. The ether phase was washed with brine and dried over Na2SO4. The solvent was evaporated in vac to give an orange solid which was purified by chromatography on silica gel eluting with acetone:hexane (2:98) to give the title compound.

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