Sodium Azide → 1-[4-(2-Azidoethyl)phenyl]ethan-1-one

HRID 1381271Notes

Reaction equation

HRID 1381271 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

HCID 33557Sodium AzideHCID 6111941-(4-(2-Bromoethyl)phenyl)ethan-1-one

Product 1

HCID 198091851-[4-(2-Azidoethyl)phenyl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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).

Sources & evidence

ORD record
ord-7a23315d1cc842c9a59c83b7f9092ac8
Source dataset
uspto-grants-1986_04
Patent number
US04585796

Reaction notes

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