Reaction #2006426

Reaction equation

methyl iodide

compound 28

4-(Benzenesulfonylamino)-phenyl Iodide

K2CO3

→

title compound

Yield 196.6%

N-Methyl-4-iodophenylbenzenesulfonamide

Yield 196.6%

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   OtherThe solvent is then removed
3. 3
   workup.ADDITIONwater was added
4. 4
   ExtractionThe resulting mixture was extracted with ethyl acetate
5. 5
   Otherthe combined organic phases were dried
6. 6
   Concentrationconcentrated
7. 7
   OtherPurification by flash chromatography

Procedure

To compound 28 (from Example 18) (500 mg, 1.39 mmol) in DMF (10 mL) were added at room temperature K2CO3 (962 mg, 6.96 mmol), followed by methyl iodide (395 mg, 2.78 mmol). The resulting reaction mixture was stirred at room temperature for 16 hours. The solvent is then removed and water was added. The resulting mixture was extracted with ethyl acetate, and the combined organic phases were dried and concentrated. Purification by flash chromatography using hexane:ethyl acetate (8:2) afforded 510 mg (98%) of the title compound as a white solid.

Source