Sodium Azide → HCID 57978188, compound

HRID 1866519Notes

Reaction equation

HRID 1866519 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:7][C:8](=[O:23])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17]OS(C)(=O)=O)[CH:11]=1)[CH3:6]>CN(C)C=O>[CH2:5]([O:7][C:8](=[O:23])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][N:1]=[N+:2]=[N-:3])[CH:11]=1)[CH3:6]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57978175HCID 57978175, compound

Product 1

HCID 57978188HCID 57978188, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium azide (2.82 g, 43.3 mmol) was added in one portion to a stirred solution of ethyl(3-{2-[(methylsulfonyl)oxy]ethyl}phenyl)acetate (Preparation 56) (6.20 g, 21.7 mmol) in N,N-dimethylformamide (400 ml) at room temperature. The reaction was heated at 60° C. for 1 hour and then allowed to cool to room temperature and the solvent removed in vacuo. Ethyl acetate (200 ml) and water (75 ml) was added and the organics separated, the aqueous was washed with ethyl acetate (2×100 ml) and the combined organics evaporated in vacuo to yield an oil that was purified by flash column chromatography on silica gel eluting with ethyl acetate:penatane (5:95, by volume) to give the title compound as a colourless oil (4.65 g). 1H NMR (400 MHz, CDCl3): δ=7.27-7.23 (1H, t), 7.17-7.12 (3H, m), 4.15-4.06 (2H, m), 3.60 (2H, s), 3.51-3.47 (2H, t), 2.87-2.84 (2H, t), 1.24-1.20 (3H, t) ppm. LRMS (electrospray): M/Z [M+NA]+256, [M−H]− 232.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent removed in vacuo
  3. additionEthyl acetate (200 ml) and water (75 ml) was added
  4. washthe organics separated, the aqueous was washed with ethyl acetate (2×100 ml)
  5. customthe combined organics evaporated in vacuo
  6. customto yield an oil that
  7. customwas purified by flash column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-b53da693e2d54ae89d0855f334a8425f
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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