Sodium Azide → 1-[4-(2-Azidoethyl)phenyl]ethan-1-one
Reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CS(C)=O>[N:13]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)=[N+:14]=[N-:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
p-(2-Bromoethyl)-acetophenone (J.A.C.S. 62, 1940, 1435) was reacted with sodium azide in dimethyl sulphoxide to give p-(2-azidoethyl)acetophenone. Oxidation with sodium hypobromide gave p-(2-azidoethyl)benzoic acid (melting point 130°-131°, from acetone/hexane) which was converted with thionyl chloride into the corresponding acid chloride. Treatment of the acid chloride with ammonia gave p-(2-azidoethyl)benzamide. Treatment with triphenylphosphine and hydrolysis gave p-(2-aminoethyl)benzamide of melting point 132°-133° (from ethanol).