ChemicalBook CAS DataBase List P-AZIDOACETOPHENONE

P-AZIDOACETOPHENONE synthesis

9synthesis methods

Product Name:P-AZIDOACETOPHENONE
CAS Number:20062-24-2
Molecular formula:C8H7N3O
Molecular Weight:161.16

99-92-3 Synthesis

99-92-3
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20062-24-2
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Yield:20062-24-2 95%

Reaction Conditions:

Stage #1: 4-Aminoacetophenonewith hydrogenchloride in water at 0 - 5; for 0.166667 h;
Stage #2: with 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy]ethyl)-1H-imidazol-3-ium dinitrite in water; for 0.166667 h;
Stage #3: with sodium azide in water at 20; for 0.166667 h;Ionic liquid;

Steps:

General procedures for the conversion of aryl amines to aryl azides

General procedure: Aniline derivative (2 mmol) was dissolved in 1 ml of 37 % HCl. The mixture was stirred at 0-5 C for 10 min, until the ammonium salt was formed and the aromatic amine disappeared. The progress of the reaction was monitored by TLC [eluent: n-hexane/ethyl acetate (90:5)]. Nitrite ionic liquid (1 mmol) was added to theaniline solution. The reaction mixture was ground mildly for 5-10 min, the diazonium salt was formed. Then, NaN3 (5 mmol, 0.326 g) was added to the mixture and stirring continued for 6-25 min at room temperature (Table 2). The mixture was filtered and washed with distilled water (3 x 8 ml) and ethyl acetate (EtOAc, 15 ml). The residue was extracted with EtOAc (3 9 10 ml) and the combined organic layer was washed with 5 % aqueous solution of NaOH (12 ml) and then it was dried over anhydrous Na2SO4 . The solvent was evaporated to afford aryl azides.

References:

Eshghi, Hossein;Bakavoli, Mehdi;Ghasemzadeh, Marjan [Research on Chemical Intermediates,2013,vol. 41,# 6,p. 3999 - 4007]