Water → HCID 54073201, compound

HRID 1579175Notes

Reaction equation

HRID 1579175 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[C:6]([N:10]=[N:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])([CH3:9])([CH3:8])[CH3:7].O>CO.CCCCC>[C:6]([N:10]=[N:11][C:12]([CH3:14])([CH3:13])[C:15](=[N:2][OH:3])[NH2:16])([CH3:9])([CH3:7])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 91297Propanenitrile, 2-[(1,1-dimethylethyl)azo]-2-methyl-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 54073201HCID 54073201, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8003PentaneSolvent

Procedure

To a mixture of 8.35 grams (0.12 moles) of hydroxylamine hydrochloride and 9.6 grams (0.12 moles) of 50% NaOH in 110 ml of 90% aqueous methanol in a 250 ml round bottom flask equipped with a magnetic stirrer and condenser was added 15.3 grams (0.1 moles) of 2-t-butylazo-2-cyanopropane (from Example I). The mixture was stirred for 72 hours at room temperature, poured into 400 ml of water and extracted with 100 ml of methylene chloride, the organic layer separated, dried over anhydrous sodium sulfate, filtered and the methylene chloride evaporated under reduced pressure leaving a soft solid. The residue was slurried in 100 ml of pentane to remove any unreacted 2-t-butylazo-2-cyanopropane, filtered and the filter cake air dried. The yield was 12.5 grams (67% yield) of a white solid having a melting point of 105°-109°C (dec.). The infrared spectrum of the product was in agreement with the structure of the desired amidoxime.

Workup

  1. customequipped with a magnetic stirrer and condenser
  2. extractionextracted with 100 ml of methylene chloride
  3. customthe organic layer separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe methylene chloride evaporated under reduced pressure
  7. customleaving a soft solid
  8. customto remove any unreacted 2-t-butylazo-2-cyanopropane
  9. filtrationfiltered
  10. customthe filter cake air dried

Sources & evidence

ORD record
ord-7010b599e23645e5addbaf9a6564529d
Source dataset
uspto-grants-1976_01
Patent number
US03931143

Reaction notes

Loading…