(E)-1-tert-Butyl-2-(2-chloro-4-methylpentan-2-yl)diazene → 2-t-Butylazo-2-phenyl-4-methylpentane

HRID 436360

Reaction equation

HRID 436360 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([N:12]=[N:13][C:14](Cl)([CH2:16][CH:17]([CH3:19])[CH3:18])[CH3:15])([CH3:11])([CH3:10])[CH3:9]>CCOCC>[C:8]([N:12]=[N:13][C:14]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:16][CH:17]([CH3:19])[CH3:18])[CH3:15])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 23344796(E)-1-tert-Butyl-2-(2-chloro-4-methylpentan-2-yl)diazeneHCID 178506676HCID 178506676, compound

Product 1

HCID 233447602-t-Butylazo-2-phenyl-4-methylpentane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

To a clean, dry 250 ml. round bottom 4 neck flask equipped with a magnetic stirrer, thermometer, condenser and addition funnel, which was being purged with nitrogen was added an ether solution containing .06 moles of phenyllithium. The solution was cooled to 5° C. and a solution of 10.25 g. (.05 moles) of 2-t-butylazo-2-chloro-4-methylpentane in 50 ml. ether was added dropwise over 1/2 hour. After the addition was complete, the reaction was warmed to 20° C. and stirred for 1/2 hour. The excess phenyllithium was destroyed with wet ether and the reaction mixture poured into 200 ml. water. The ether layer was separated, dried over anhydrous sodium sulfate, filtered and the ether removed on a rotating evaporator leaving 11.9 g. (96%) of a liquid. The infrared spectrum was in agreement with the structure of the title compound.

Workup

  1. customTo a clean, dry 250 ml
  2. customround bottom 4 neck flask equipped with a magnetic stirrer
  3. additionthermometer, condenser and addition funnel
  4. customwhich was being purged with nitrogen
  5. additionwas added an ether solution
  6. additionAfter the addition
  7. temperaturethe reaction was warmed to 20° C.
  8. customThe excess phenyllithium was destroyed with wet ether
  9. additionthe reaction mixture poured into 200 ml
  10. customThe ether layer was separated
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customthe ether removed on a rotating evaporator
  14. customleaving 11.9 g

Sources & evidence

ORD record
ord-9ed3a7ca4f3044e29c847783ef68a88a
Source dataset
uspto-grants-1977_02
Patent number
US04008273

Linked notes

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