Reaction #4302

Reaction equation

2-chloroethyl phenyl sulfide

potassium iodide

isopropylamine

→

white crystalline solid

Yield 76.9%

N-[2-(Phenylthio)ethyl]-2-propanamine hydrochloride

Yield 76.9%

Conditions

Workup

1. 1
   OtherThe solvent was removed in vacuo
2. 2
   Otherthe residue was partitioned between methylene chloride and dilute sodium hydroxide
3. 3
   ExtractionThe methylene chloride solution was extracted with dilute sulfuric acid
4. 4
   ExtractionThe acidic extract
5. 5
   Extractionthe basic solution was extracted with methylene chloride
6. 6
   DryingThe methylene chloride solution was dried over magnesium sulfate
7. 7
   Otherthe solvent was removed in vacuo
8. 8
   Otherto give an oil
9. 9
   Otherthe salt was recrystallized from methanol-ether

Procedure

A solution of 25 g (0.145 mole) of 2-chloroethyl phenyl sulfide and 1 g (0.006 mole) of potassium iodide in 500 ml of isopropylamine was heated in a bomb at 120° C. for 24 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was extracted with dilute sulfuric acid. The acidic extract was made basic with 50% sodium hydroxide, and the basic solution was extracted with methylene chloride. The methylene chloride solution was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil. This was converted to the hydrochloride salt, and the salt was recrystallized from methanol-ether to give 25.77 g (76.9%) of white crystalline solid, m.p. 124.5°-125.5° C.

Source