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

HRID 442317Notes

Reaction equation

HRID 442317 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 241BenzeneSolvent

Procedure

Into a 25 ml round bottom flask was weighed 5 grams (0.0237 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° C. ± 2° C. (protected from the atmosphere by a CaCl2 tube). At the end of the stirring period the benzene and excess thionyl chloride were evaporated under reduced pressure 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
  4. customAt the end of the stirring period the benzene and excess thionyl chloride were evaporated under reduced pressure

Sources & evidence

ORD record
ord-4c8fa5ccfb874159b0e7e3737d6d8746
Source dataset
uspto-grants-1977_08
Patent number
US04045427

Reaction notes

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