Dimethyl Sulfoxide → N-[2-[(4-Ethoxyphenyl)sulfonyl]ethyl]-2-propanamine hydrochloride
Reaction equation
[H-].[Na+].CS(C)=O.[CH2:7]([OH:9])[CH3:8].Cl.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:21][CH2:22][NH:23][CH:24]([CH3:26])[CH3:25])(=[O:20])=[O:19])=[CH:14][CH:13]=1>>[ClH:11].[CH2:7]([O:9][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:21][CH2:22][NH:23][CH:24]([CH3:26])[CH3:25])(=[O:19])=[O:20])=[CH:14][CH:13]=1)[CH3:8]Participants
Procedure
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 (obtained in Preparation 23) 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 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.
Workup
- temperatureThe mixture was heated at 120°-140° C. for 1 hr
- customthe solvent was removed in vacuo
- customThe residue was partitioned between methylene chloride and dilute sodium hydroxide
- dry with materialThe methylene chloride solution was dried over magnesium sulfate
- customthe solvent removed in vacuo
- dissolutionThe residue was dissolved in methanol
- additionan excess of ethereal hydrogen chloride was added
- additionether was added
- customA white solid precipitated in amount of 14.92 g (69.2%), m.p. 168°-170° C.
Sources & evidence
- ORD record
- ord-51349f423322443eb19b7cbe24f5ddfa
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04895840
Reaction notes
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