Sodium Azide → 3-(3-Methoxy-4-methylphenyl)acryloyl azide

HRID 1366751Notes

Reaction equation

HRID 1366751 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12](Cl)=[O:13])[CH:6]=[CH:7][C:8]=1[CH3:9].[N-:15]=[N+:16]=[N-:17].[Na+]>CC(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]([N:15]=[N+:16]=[N-:17])=[O:13])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 866129803-(3-Methoxy-4-methylphenyl)acryloyl chloride

Product 1

HCID 866129813-(3-Methoxy-4-methylphenyl)acryloyl azide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

The 3-(3-methoxy-4-methylphenyl)acryloyl chloride was dissolved in acetone (800 ml). The resulting solution was added slowly (15 min) at 0° C. to a mixture of sodium azide (13 g) in water (100 ml) and acetone (100 ml) while vigorously stirring and cooling with an ice-bath. After addition was complete the reaction mixture was stirred at 0° C. for 90 minutes while vigorously stirring. The reaction mixture was then poured out on ice-water (300ml). After stirring for 15 minutes the mixture was filtered and the solid residue washed with excess water. The remaining solid residue was dissolved in dichloromethane (45 ml). The liberated water was removed with a separatory funnel. The dichloromethane layer was dried with Na2SO4 and filtered to give a dichloromethane solution of 3-(3-methoxy-4-methylphenyl)acryloyl azide for immediate use in the next step.

Workup

  1. additionThe resulting solution was added slowly (15 min) at 0° C.
  2. temperaturecooling with an ice-bath
  3. additionAfter addition
  4. stirringwas stirred at 0° C. for 90 minutes
  5. stirringwhile vigorously stirring
  6. additionThe reaction mixture was then poured out on ice-water (300ml)
  7. stirringAfter stirring for 15 minutes the mixture
  8. filtrationwas filtered
  9. washthe solid residue washed with excess water
  10. dissolutionThe remaining solid residue was dissolved in dichloromethane (45 ml)
  11. customThe liberated water was removed with a separatory funnel
  12. dry with materialThe dichloromethane layer was dried with Na2SO4
  13. filtrationfiltered

Sources & evidence

ORD record
ord-a64e55e40d674613a405dc501ceb21cb
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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