Sodium Azide → HCID 22406562, compound

HRID 440278Notes

Reaction equation

HRID 440278 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:12][C:11]([C:13](O)=[O:14])=[C:10]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+]>CC(C)=O.O.C(N(CC)CC)C.ClC(OCC)=O>[C:1]([O:5][C:6]([C:8]1[S:12][C:11]([C:13]([N:21]=[N+:22]=[N-:23])=[O:14])=[C:10]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 2

HCID 33557Sodium AzideHCID 22406563HCID 22406563, compound

Product 1

HCID 22406562HCID 22406562, compoundYield 99,882.203%

Reagents, catalysts & solvents 4

HCID 8471TriethylamineCatalystHCID 10928Ethyl chloroformateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl-2-carboxy-3-tert-butoxy-5-thiophenecarboxylate (3 g, 0.01 mmol) in dry acetone (100 ml) was treated, at 0° C., with triethylamine (1.7 ml, 0.012 mmol) added dropwise. The mixture was stirred for 15 minutes and ethyl chloroformate (1.25 ml, 0.013 mmol) added dropwise, at 0° C. After 30 minutes, sodium azide (1.1 g, 0.017 mmol) in water (5 ml) was slowly added, at 0° C. After 4 hours, stirring at ambient temperature, the reaction mixture was filtered and the solvent evaporated. The oily residue was dissolved in CH2Cl2, and the solution washed (2×) with water, dried over MgSO4 and the solvent evaporated to give title compound (3.25 g, 100%).

Workup

  1. additionadded dropwise
  2. waitAfter 30 minutes
  3. waitAfter 4 hours
  4. stirringstirring at ambient temperature
  5. filtrationthe reaction mixture was filtered
  6. customthe solvent evaporated
  7. dissolutionThe oily residue was dissolved in CH2Cl2
  8. washthe solution washed (2×) with water
  9. dry with materialdried over MgSO4
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-b488c28fafab4d019185f41b3a8005bf
Source dataset
uspto-grants-1996_05
Patent number
US05519015

Reaction notes

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