Water → HCID 20368600, compound

HRID 1287981Notes

Reaction equation

HRID 1287981 reaction equation
[C:1]([N:5]=[N:6][C:7]([S:13][CH2:14][CH2:15][OH:16])([CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:23]([N:27]=[N:28][C:29]([C:36]#[N:37])([CH3:35])[CH2:30][CH2:31][C:32](Cl)=[O:33])([CH3:26])([CH3:25])[CH3:24].O>CCCCC>[C:23]([N:27]=[N:28][C:29]([C:36]#[N:37])([CH3:35])[CH2:30][CH2:31][C:32]([O:16][CH2:15][CH2:14][S:13][C:7]([N:6]=[N:5][C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:8])[CH2:9][CH:10]([CH3:11])[CH3:12])=[O:33])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 152740244-[(E)-tert-Butyldiazenyl]-4-cyanopentanoyl chlorideHCID 2036859457909-40-7

Product 1

HCID 20368600HCID 20368600, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6.5 grams (.0264 moles) of 2-t-butylazo-2-(β-hydroxyethylthio)-4-methylpentane and 2.5 grams (.031 moles) of pyridine in 50 ml of pentane in a beaker was added 5.75 grams (.025 moles) of 4-t-butylazo-4-cyanovaleryl chloride dropwise while holding the reaction temperature at 25° C ± 2° C. After the addition was complete, the reaction was stirred an additional 1/2 hour at 25° C, 50 ml of water added and the pentane layer separated. The pentane layer was successively washed with 25 ml of 10% HCl, 25 ml of water and 25 ml of 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered and the pentane evaporated under reduced pressure to leave a viscous tan liquid weighing 7.3 grams (66% yield). The product was purified by chromatographing it over alumina and eluting it with pentane. Evaporation of the pentane left a yellow viscous liquid whose infrared spectrum was in agreement with the structure of the desired product.

Workup

  1. customat 25° C ± 2° C
  2. additionAfter the addition
  3. customthe pentane layer separated
  4. washThe pentane layer was successively washed with 25 ml of 10% HCl, 25 ml of water and 25 ml of 10% NaHCO3 solution
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe pentane evaporated under reduced pressure
  8. customto leave a viscous tan liquid
  9. customThe product was purified by chromatographing it over alumina
  10. washeluting it with pentane
  11. customEvaporation of the pentane
  12. waitleft a yellow viscous liquid whose infrared spectrum

Sources & evidence

ORD record
ord-f21bd10a71ff427bacb240027022b108
Source dataset
uspto-grants-1976_10
Patent number
US03987024

Reaction notes

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