4-Chlorobenzaldehyde → 4-(Pyridin-2-ylsulfanyl)benzaldehyde

HRID 2413357Notes

Reaction equation

HRID 2413357 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[SH:7].Cl[C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)P(N(C)C)(N(C)C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 11430Potassium CarbonateHCID 178418616HCID 178418616, compound

Product 1

HCID 133925764-(Pyridin-2-ylsulfanyl)benzaldehydeYield 42.2%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 18.4 g of 2-pyridinethiol, 23.2 g of 4-chlorobenzaldehyde, 40 g of potassium carbonate and 100 ml of hexamethylphosphoramide was heated at a temperature of 140° C. for 4 hours. After cooling, the mixture was filtered and the filtrate was concentrated. The resulting oily substance was dissolved in diethyl ether and the solution was washed successively with an aqueous solution of sodium hydroxide and water, and dried over magnesium sulfate. The solvent was distilled off and the resulting oily substance was distilled under reduced pressure to obtain 15 g (42% yield) of 4-(2-pyridylthio)benzaldehyde as a colorless oil having a boiling point of 136° C./2 mmHg.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe resulting oily substance was dissolved in diethyl ether
  5. washthe solution was washed successively with an aqueous solution of sodium hydroxide and water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. distillationthe resulting oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-764d786d4b5c475098dedf563366506b
Source dataset
uspto-grants-1985_01
Patent number
US04496735

Reaction notes

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