Sodium Azide → HCID 20276024, compound

HRID 370462Notes

Reaction equation

HRID 370462 reaction equation
[CH:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[O:6][C:7]1C(C(C)C)=C(S([O-])(=O)=O)C=[CH:9][C:8]=1C)([CH3:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C)C=O>[CH:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[O:6][CH2:7][CH:8]([N:25]=[N+:26]=[N-:27])[CH3:9])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86740174HCID 86740174, compound

Product 1

HCID 20276024HCID 20276024, compoundYield 164.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 21.0 g of 2-(2-isopropylphenoxy)-1-methylethyl-p-toluenesulfonate, 3.9 g of sodium azide and N,N-dimethylformamide was heated at 70° to 75° C. for 5 hr. with stirring. Upon completion of the reaction, the mixture was extracted with ethyl acetate; the extract was washed consecutively with water and saturated saline; and subsequently dried with anhydrous sodium sulfate. The solvent was thereafter distilled off under reduced pressure and yielded 21.6 g of 2-(2-isopropylphenoxy)-1-methylethylazide.

Workup

  1. temperaturewas heated at 70° to 75° C. for 5 hr
  2. customUpon completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe extract was washed consecutively with water and saturated saline
  5. dry with materialand subsequently dried with anhydrous sodium sulfate
  6. distillationThe solvent was thereafter distilled off under reduced pressure

Sources & evidence

ORD record
ord-648c307ec2f84152bacb3566db44ce02
Source dataset
uspto-grants-1985_07
Patent number
US04526893

Reaction notes

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