Reaction #4291

Reaction equation

N-[2-[(3,4-dichlorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester

→

white crystalline product

Yield 32.4%

N-[2-[(3,4-Dichlorophenyl)sulfonyl]ethyl]-2-propanamine

Yield 32.4%

Solvents

HBr

Conditions

Workup

1. 1
   Temperatureat reflux for 12 hr
2. 2
   Extractionextracted with chloroform
3. 3
   ExtractionThe chloroform layer was extracted with 1N sulfuric acid
4. 4
   ExtractionThe sulfuric acid layer was extracted with chloroform
5. 5
   Otherevaporated to an oil
6. 6
   OtherA portion of the oil was reacted with ethereal hydrogen chloride

Procedure

A solution of 44.27 g (0.107 mole of N-[2-[(3,4-dichlorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester in 300 ml of 48% HBr was heated at reflux for 12 hr. The reaction mixture was cooled to room temperature, made alkaline with 50% sodium hydroxide-ice and extracted with chloroform. The chloroform layer was extracted with 1N sulfuric acid. The sulfuric acid layer was extracted with chloroform and the chloroform layers combined and evaporated to an oil, the free base of the title compound. A portion of the oil was reacted with ethereal hydrogen chloride to give an overall yield of 32.4% white crystalline product, m.p. 219°-221° C.

Source