반응 #4308

반응 방정식

ethanol

sodium hydride

dimethyl sulfoxide

N-[2-(4-chlorophenylsulfonyl)ethyl]-2-propanamine hydrochloride

→

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

반응 조건

후처리

1. 1
   온도The mixture was heated at 120°-140° C. for 1 hr
2. 2
   기타the solvent was removed in vacuo
3. 3
   기타The residue was partitioned between methylene chloride and dilute sodium hydroxide
4. 4
   건조The methylene chloride solution was dried over magnesium sulfate
5. 5
   기타the solvent was removed in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in methanol
7. 7
   workup.ADDITIONan excess of ethereal hydrogen chloride was added
8. 8
   workup.ADDITIONether was added
9. 9
   기타A white solid precipitated in amount of 14.92 g (69.2%), m.p. 168°-170° C.

실험 절차

To a suspension of 6.6 g of a 60% dispersion of sodium hydride in oil (0.165 mole) in 300 mole of dimethyl sulfoxide was added 7.5 g (0.163 mole) of absolute ethanol. The mixture was stirred at room temperature for 0.5 hr, and 20.8 g (0.080 mole) of N-[2-(4-chlorophenylsulfonyl)ethyl]-2-propanamine hydrochloride was added as a solid. The mixture was heated at 120°-140° C. for 1 hr, and the solvent was removed in vacuo. The residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in methanol, an excess of ethereal hydrogen chloride was added, and ether was added. A white solid precipitated in amount of 14.92 g (69.2%), m.p. 168°-170° C.

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