반응 #4293

반응 방정식

N-[2-[(4-fluorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester

sodium hydroxide

methylene chloride

→

title compound

N-[2-[(4-Fluorophenyl)sulfonyl]ethyl]-2-propanamine hydrochloride

용매

HBr

methanol

반응 조건

후처리

1. 1
   온도at reflux for 8 hr
2. 2
   온도The reaction mixture was cooled with ice
3. 3
   추출The aqueous phase was extracted with chloroform
4. 4
   추출The chloroform layer was extracted with sodium hydroxide
5. 5
   기타Evaporation of the chloroform layer
6. 6
   기타gave an oil residue
7. 7
   추출the solution extracted with 1N sulfuric acid
8. 8
   workup.ADDITIONwith a mixture of ice and 50% sodium hydroxide solution
9. 9
   추출extracted with chloroform
10. 10
    기타Removal of chloroform
11. 11
    기타gave an oil

실험 절차

A solution of 60.25 g (0.165 mole) of N-[2-[(4-fluorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester in 400 ml of 48% HBr was heated at reflux for 8 hr. The reaction mixture was cooled with ice and made alkaline with 50% sodium hydroxide. The aqueous phase was extracted with chloroform. The chloroform layer was extracted with sodium hydroxide. Evaporation of the chloroform layer gave an oil residue. The oil was dissolved in methylene chloride and the solution extracted with 1N sulfuric acid. The acidic layer was made alkaline with a mixture of ice and 50% sodium hydroxide solution and extracted with chloroform. Removal of chloroform gave an oil, the free base of the title compound, which was dissolved in methanol and reacted with ethereal hydrogen chloride to give the hydrochloride salt. On recrystallization from methanol-diethyl ether a white crystalline product; m.p. 168°-169° C. in 31.1% yield was obtained.

출처