Phosphorus pentachloride → HCID 21537190, compound

HRID 1578574Notes

Reaction equation

HRID 1578574 reaction equation
[C:1]([N:6]=[N:7][C:8]([C:15]#[N:16])([CH3:14])[CH2:9][CH2:10][C:11](O)=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:18]>CCCCC>[C:1]([N:6]=[N:7][C:8]([C:15]#[N:16])([CH3:14])[CH2:9][CH2:10][C:11]([Cl:18])=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 21537182HCID 21537182, compound

Product 1

HCID 21537190HCID 21537190, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a stirred slurry of 10 grams (.0443 moles) of 4-t-amylazo-4-cyanovaleric acid in 50 mls. of pentane in a 100 ml. flask was added 9.37 grams(.045 moles) of PCl5 over a 10 minute period. After the addition was complete, the reaction was stirred at room temperature for another 50 minutes and poured into 100 mls. of ice water. The pentane layer was separated, washed with 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered and the pentane evaporated to leave 9.0 grams (84% yield) of 4-t-amylazo-4-cyanovaleryl chloride.

Workup

  1. additionAfter the addition
  2. additionpoured into 100 mls
  3. customThe pentane layer was separated
  4. washwashed with 10% NaHCO3 solution
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe pentane evaporated

Sources & evidence

ORD record
ord-5da6b720e70a4a518088cb4147f667c0
Source dataset
uspto-grants-1976_02
Patent number
US03937761

Reaction notes

Loading…