Reaction #4835

Reaction equation

propine

2-iodophenylsulfonamide

P(C6H5)3

→

phenylsulfonamide

Solvents

dimethylformamide

triethylamine

Conditions

Workup

1. 1
   Otheris completely reacted
2. 2
   FiltrationThe reaction mixture is filtered
3. 3
   Concentrationthe residue is concentrated in vacuo
4. 4
   OtherThe precipitate is isolated
5. 5
   Otherdried
6. 6
   OtherRecrystallisation from ethyl acetate/hexane

Procedure

To a solution of 28.3 g (0.1 mole) of 2-iodophenylsulfonamide in 350 ml of dimethylformamide and 100 ml of triethylamine are added 1.0 g of palladium dichloro-bis(triphenylphosphite) complex, PdCl2 [P(C6H5)3 ]2, and 0.5 g of copper(I) iodide (CuI). Gaseous propine is then introduced into this solution until the starting material is completely reacted. The reaction mixture is filtered and the residue is concentrated in vacuo and then taken up in water. The precipitate is isolated and dried. Recrystallisation from ethyl acetate/hexane yields 15.6 g (80%) of 2-propyn-1-yl)phenylsulfonamide with a melting point of 147°-149° C.

Source