Sodium Azide → HCID 20245092, compound

Reaction equation

[O:1]([CH2:8][CH2:9][C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CC(C)=O.O>[O:1]([CH2:8][CH2:9][C:10]([N:13]=[N+:14]=[N-:15])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Procedure

Phenoxypropionyl chloride (9.23 g, 0.05 mol) is dissolved in 100 ml acetone and cooled with an ice bath as sodium azide (3.6 g, 0.055 mol) in 10 ml water is added dropwise. After addition is completed, the reaction mixture is warmed to room temperature and stirred for 30 minutes. The solution is decanted and concentrated. The residue is dissolved in 100 ml ether and washed with saturated sodium bicarbonate and brine. The organic phase is separated, dried (MgSO4) and concentrated to give 6.52 g (68.0% yield) of phenoxypropionyl azide as a yellow oil which solidifies on cooling. IR (KBr) cm-1 : 2137 (N3), 1718 (C=O); 1H nmr (CDCl3) δ: 7.31 (m, 2H, phenyl H), 6.98 (t, 1H, J=7.5 Hz, phenyl H), 6.92 (m, 2H, phenyl H), 4.26 (t, 3H, J=6.3 Hz, CH2O), 2.84 (t, 3H, J=6.3 Hz, CH2C=O); 13C nmr (CDCl3) δ: 178.0, 159.0, 129.5(2C), 121.2, 114.7(2C), 62.9, 36.9.