Water → HCID 54424487, compound

HRID 1834339Notes

Reaction equation

HRID 1834339 reaction equation
[OH2:1].Cl.[NH2:3]O.[OH-].[Na+].[CH3:7][CH:8]([N:13]=[N:14][C:15]([C:18]#[N:19])([CH3:17])[CH3:16])[CH2:9][CH:10]([CH3:12])[CH3:11]>CO>[CH3:7][CH:8]([N:13]=[N:14][C:15]([CH3:16])([CH3:17])[C:18](=[N:3][OH:1])[NH2:19])[CH2:9][CH:10]([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 21386979HCID 21386979, compound

Product 1

HCID 54424487HCID 54424487, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml of water and 6.45 grams (0.0926 moles) of hydroxylamine hydrochloride in a 250 ml 3-neck round bottom flask equipped with a magnetic stirrer, air-cooled condenser, thermometer, and immersed in an ice bath was slowly added 7.42 grams (0.0926 moles) of 50% sodium hydroxide, followed by 100 ml of methanol. To this stirred mixture was added 16.4 grams (.0906 moles) of 2-(1,3-dimethyl-butylazo)-2-cyanopropane (from Example 4-a-4). The ice bath was removed and the flask stoppered and the reaction mixture stirred for 11/2 hours and allowed to stand over the weekend at room temperature. The insolubles were filtered off and the methanol filtrate was poured into 150 ml water and the product extracted with 100 ml of pentane. The pentane solution was washed twice with 100 ml portions of water, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure on a rotating evaporator. The product was a yellow liquid and weighed 8.8 grams (46% crude yield). The infrared spectrum of the product was in agreement with the structure of 2-(1,3-dimethylbutylazo)- 2-methylpropionamidoxime (strong broad NH and OH bands at 3150-3450 cm-1, a strong imino band at 1750 cm-1 and the absence of the cyano band of the starting material at 2225 cm-1).

Workup

  1. temperatureair-cooled condenser
  2. customthermometer, and immersed in an ice bath
  3. customThe ice bath was removed
  4. customto stand over the weekend at room temperature
  5. filtrationThe insolubles were filtered off
  6. additionthe methanol filtrate was poured into 150 ml water
  7. extractionthe product extracted with 100 ml of pentane
  8. washThe pentane solution was washed twice with 100 ml portions of water
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe pentane evaporated under reduced pressure on a rotating evaporator

Sources & evidence

ORD record
ord-22b1f152eeaa423da8ecd9f9bc4abf96
Source dataset
uspto-grants-1978_01
Patent number
US04069377

Reaction notes

Loading…