Water → HCID 21567574, compound

HRID 1579173Notes

Reaction equation

HRID 1579173 reaction equation
[OH-].[Na+].[C:3]([N:7]=[N:8][C:9]([C:17]#[N:18])([CH3:16])[CH2:10][C:11]([O:13]CC)=[O:12])([CH3:6])([CH3:5])[CH3:4].O>CO>[C:3]([N:7]=[N:8][C:9]([C:17]#[N:18])([CH3:16])[CH2:10][C:11]([OH:13])=[O:12])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21567571HCID 21567571, compound

Product 1

HCID 21567574HCID 21567574, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5.6 grams (0.07 moles) of 50% sodium hydroxide in 20 ml of methanol was added 11.25 grams (0.05 moles) of ethyl 3-t-butylazo-3-cyanobutyrate (from Example XXVI). The reaction mixture was stirred for 1 hour at room temperature, poured into 100 ml of water and extracted with 50 ml of pentane to remove any unsaponified ester. The aqueous layer was separated, acidified with HCl to a pH of 1. A solid formed which was filtered off, washed with water and pentane and air dried. The solid weighed 6.0 grams. The infrared spectrum of a nujol mull of the solid was in agreement with the structure of 3-t-butylazo-3-cyanobutyric acid. The melting point was 136°-145°C (dec.).

Workup

  1. extractionextracted with 50 ml of pentane
  2. customto remove any unsaponified ester
  3. customThe aqueous layer was separated
  4. customA solid formed which
  5. filtrationwas filtered off
  6. washwashed with water and pentane and air
  7. customdried

Sources & evidence

ORD record
ord-6a4d619c9ee44eecb3f209f742ddc8da
Source dataset
uspto-grants-1976_01
Patent number
US03931143

Reaction notes

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