Triethylamine → 1-t-Butylazo-1-chlorocyclohexane

HRID 436728

Reaction equation

HRID 436728 reaction equation
[C:1]([NH:5][N:6]=[C:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:20]Cl>CCCCC>[C:1]([N:5]=[N:6][C:7]1([Cl:20])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24526Chlorine2×HCID 169919Cyclohexanone, 2-(1,1-dimethylethyl)hydrazone

Product 1

HCID 233447841-t-Butylazo-1-chlorocyclohexane

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a stirred solution of 252 grams (1.5 moles) of cyclohexanone t-butylhydrazone and 160 grams (1.5 moles) of triethylamine in 1200 ml pentane in a 3 liter 4 neck flask equipped with a mechanical stirrer, thermometer and gas inlet tube, was added 107 grams (1.5 moles) of chlorine gas, holding the temperature at -10° to 0° C. After the chlorine addition was complete, the reaction mixture was stirred an additional 15 minutes and the insoluble triethylamine hydrochloride filtered off. The filter cake was washed with an additional 300 ml pentane and the filtrate stripped of pentane under reduced pressure. The yield of 1-t-butylazo-1-chlorocyclohexane was 266 grams (87.5% crude yield).

Workup

  1. customat -10° to 0° C
  2. filtrationthe insoluble triethylamine hydrochloride filtered off
  3. washThe filter cake was washed with an additional 300 ml pentane

Sources & evidence

ORD record
ord-cec35b8d25eb457380862f8bea1cbeed
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Linked notes

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