Thionyl Chloride → 4-[(E)-tert-Butyldiazenyl]-4-cyanopentanoyl chloride

HRID 973282Notes

Reaction equation

HRID 973282 reaction equation
[C:1]([N:5]=[N:6][C:7]([C:14]#[N:15])([CH3:13])[CH2:8][CH2:9][C:10](O)=[O:11])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:18])=O>C1C=CC=CC=1>[C:1]([N:5]=[N:6][C:7]([C:14]#[N:15])([CH3:13])[CH2:8][CH2:9][C:10]([Cl:18])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 91299Pentanoic acid, 4-cyano-4-(2-(1,1-dimethylethyl)diazenyl)-

Product 1

HCID 152740244-[(E)-tert-Butyldiazenyl]-4-cyanopentanoyl chlorideYield 98.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Into a 25 ml round bottom flask was weighed 5 grams (.0237 mole) of 4-t-butylazo-4-cyanovaleric acid and then 15 ml of benzene and 2 ml of thionyl chloride were added. The acid dissolved and the solution was stirred for 4 hours at 25° ±2° C (protected from the atmosphere by a CaCl2 tube). At the end of the stirring period the benzene and excess leaving 5.35 grams (98.8% yield) of 4-t- butylazo-4-cyanovaleryl chloride.

Workup

  1. customInto a 25 ml round bottom flask was weighed
  2. dissolutionThe acid dissolved
  3. customprotected from the atmosphere by a CaCl2 tube

Sources & evidence

ORD record
ord-0459f62506ae4c61bc7076e8e0125f41
Source dataset
uspto-grants-1977_10
Patent number
US04055714

Reaction notes

Loading…