Sodium Azide → HCID 20245092, compound

HRID 1075397Notes

Reaction equation

HRID 1075397 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

5

Reactant 2

HCID 33557Sodium AzideHCID 1199233-Phenoxypropionyl chloride

Product 1

HCID 20245092HCID 20245092, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

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.

Workup

  1. additionis added dropwise
  2. additionAfter addition
  3. customThe solution is decanted
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in 100 ml ether
  6. washwashed with saturated sodium bicarbonate and brine
  7. customThe organic phase is separated
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3afe03b625184ce28a002e0dde3435ba
Source dataset
uspto-grants-1999_05
Patent number
US05900485

Reaction notes

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