4-Chlorophenol → HCID 19979379, compound

HRID 1461763Notes

Reaction equation

HRID 1461763 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[N:21]=[C:20]([CH:22]([CH3:24])[CH3:23])[C:19]([N+:25]([O-:27])=[O:26])=[C:18]([CH:28]([CH3:30])[CH3:29])[CH:17]=1.[Cl-].[Na+]>CS(C)=O.C1(C)C=CC=CC=1.O>[CH:22]([C:20]1[C:19]([N+:25]([O-:27])=[O:26])=[C:18]([CH:28]([CH3:30])[CH3:29])[CH:17]=[C:16]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:21]=1)([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 46844-ChlorophenolHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 19979377HCID 19979377, compound

Product 1

HCID 19979379HCID 19979379, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

0.77 g of 4-chlorophenol and 1.00 g of potassium carbonate are suspended in 6 ml of dimethyl sulfoxide and the suspension is heated for 1 hour at +60° C.; a solution of 1.46 g of 6-chloro-2,4-diisopropyl-3-nitropyridine in 4 ml of dimethyl sulfoxide is then added dropwise. When the addition is complete, the mixture is heated for 1 hour at +120° C. with vigorous stirring. After cooling, the reaction mixture is poured onto 100 ml of water and 50 ml of toluene and then saturated with sodium chloride. The resulting suspension is filtered over diatomaceous earth and the filtrate is extracted with toluene. The organic phase is dried over magnesium sulfate and the solvent is evaporated. The residue is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 1:30). 2,4-Diisopropyl-6-(4-chlorophenoxy)-3-nitropyridine is obtained in the form of a light-yellow crystalline powder, m.p. 102°-104° C.

Workup

  1. temperaturethe suspension is heated for 1 hour at +60° C.
  2. additionWhen the addition
  3. temperaturethe mixture is heated for 1 hour at +120° C. with vigorous stirring
  4. temperatureAfter cooling
  5. filtrationThe resulting suspension is filtered over diatomaceous earth
  6. extractionthe filtrate is extracted with toluene
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. customthe solvent is evaporated
  9. customThe residue is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 1:30)

Sources & evidence

ORD record
ord-ca3fe4f00e26488f81eae6f297fa5b07
Source dataset
uspto-grants-1991_12
Patent number
US05077304

Reaction notes

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