Pyridine → Ether isopropyl ether

HRID 2107036Notes

Reaction equation

HRID 2107036 reaction equation
[C:1]1(NN)[CH:6]=[CH:5]C=CC=1.N1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:15]1([C:21](Cl)=[O:22])CCCCC1>CN(C=O)C>[CH:11]([O:22][CH:6]([CH3:5])[CH3:1])([CH3:12])[CH3:10].[CH2:21]([O:22][CH2:13][CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7516PhenylhydrazineHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 21919906Ether isopropyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0-5° C.) solution of 43.2 g (0.4mol) phenylhydrazine and 35.2 g (0.44 mol) pyridine in 300 ml DMF were added slowly 51 g (0.35 mol) cyclohexane carboxylic acid chloride. The solution was stirred 30 mn more after the end of the addition and concentrated under vacuum. The residue was poured in 300 ml water and stirred 30 mn. Filtration, washing with water and drying led to 74.5 g (98%) of the desired compound. The compound contained traces of starting material and was used without further purification. An analytical sample was obtained from isopropyl ether/ethyl ether

Workup

  1. additionmore after the end of the addition
  2. concentrationconcentrated under vacuum
  3. additionThe residue was poured in 300 ml water
  4. stirringstirred 30 mn
  5. filtrationFiltration
  6. washwashing with water
  7. customdrying
  8. customwas used without further purification

Sources & evidence

ORD record
ord-37fa4838081a4abe9dc9dd6587d50b4a
Source dataset
uspto-grants-1990_06
Patent number
US04933336

Reaction notes

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