Sodium Hydroxide → HCID 20318248, compound

HRID 866737Notes

Reaction equation

HRID 866737 reaction equation
[C:1]([N:5]=[N:6][C:7]([N:18]=[N+:19]=[N-:20])([CH3:17])[CH2:8][CH2:9][C:10]([O:12]CCCC)=[O:11])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>>[C:1]([N:5]=[N:6][C:7]([N:18]=[N+:19]=[N-:20])([CH3:17])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 20318260HCID 20318260, compound

Product 1

HCID 20318248HCID 20318248, compoundYield 94.7%

Conditions

Temperature
80 °C

Procedure

A mixture of 73.3 grams (0.223 moles) of n-butyl 4-t-butylazo-4-azidovalerate and 38.4 grams (0.24 moles) of 25% NaOH in a 250 ml. round bottom flask were warmed to 80° C in an oil bath. The mixture was stirred for 90 minutes at 80° C and then cooled to room temperature. It was then poured into 200 ml. of water and the aqueous solution extracted with 50 ml. of methylene chloride and the methylene chloride layer discarded. The aqueous solution was acidified with concentration HCl to a pH of 3 and then extracted with pentane. The pentane solution was dried over anhydrous sodium sulfate, filtered and the pentane evaporated to leave 48.0g (92.4% yield) of a light yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. additionIt was then poured into 200 ml
  3. extractionof water and the aqueous solution extracted with 50 ml
  4. concentrationThe aqueous solution was acidified with concentration HCl to a pH of 3
  5. extractionextracted with pentane
  6. dry with materialThe pentane solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe pentane evaporated

Sources & evidence

ORD record
ord-abe4f71ea7894392838cd56796bb40a9
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

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