Sodium Azide → HCID 20318260, compound

HRID 866736Notes

Reaction equation

HRID 866736 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([N:9]=[N:10][C:11](Cl)([CH3:21])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15])([CH3:8])([CH3:7])[CH3:6]>CO>[C:5]([N:9]=[N:10][C:11]([N:1]=[N+:2]=[N-:3])([CH3:21])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2031823458496-97-2

Product 1

HCID 20318260HCID 20318260, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 20.2 grams (0.31 moles) of sodium azide in 200 ml. of 70% aqueous methanol cooled in an ice bath, was added dropwise 80.0 grams (.29 moles) of n-butyl 4-t-butylazo-4-chlorovalerate (prepared as in Example XX) over a 20 minute period. After the addition was complete the reaction mixture was stirred for 1 hour at 15° C. It was then poured into 500 ml. of water and extracted with pentane. The pentane solution was washed with water, saturated NaHCO3 solution, water, dried over anhydrous sodium sulfate, filtered and the pentane evaporated to leave 77 grams (93.7% yield) of the desired product.

Workup

  1. additionAfter the addition
  2. additionIt was then poured into 500 ml
  3. extractionof water and extracted with pentane
  4. washThe pentane solution was washed with water, saturated NaHCO3 solution, water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe pentane evaporated

Sources & evidence

ORD record
ord-97049241ea534978990fb272bef9beda
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

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