Sulfuryl chloride → 2-[3-Chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid

HRID 1732997Notes

Reaction equation

HRID 1732997 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1.S(Cl)([Cl:21])(=O)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([Cl:21])[CH:10]=[N:9]1

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 203035002-[3-Chloro-4-(pyrazol-1-yl)phenyl]propionic acid

Product 1

HCID 203034102-[3-Chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acidYield 91.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2.5 g (10 mmoles) of 2-[3-chloro-4-(pyrazol-1-yl)phenyl]propionic acid are dissolved in 30 ml of methylene chloride. A solution of 2.01 g (15 mmoles) of sulfuryl chloride in 10 ml of chloroform is added dropwise, with cooling to the resulting solution; heating is effected gradually to room temperature; and this is followed by boiling under reflux for 2 hours. The reaction solution is allowed to cool; the solvent is distilled off; 50 ml of 2 N solution of sodium hydroxide are added to the thus-obtained residue, and boiling up is effected for a few minutes. The reaction solution is extracted with diethyl ether and then acidified with hydrochloric acid. After renewed extraction with diethyl ether, the combined ether phases are dried and evaporated to produce 2.6 g (90% of theory) of 2-[3-chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid, m.p. 102° to 103° C.

Workup

  1. temperaturewith cooling to the resulting solution
  2. temperatureheating
  3. customis effected gradually to room temperature
  4. temperatureunder reflux for 2 hours
  5. temperatureto cool
  6. distillationthe solvent is distilled off
  7. addition50 ml of 2 N solution of sodium hydroxide are added to the thus-obtained residue
  8. waitboiling up is effected for a few minutes
  9. extractionThe reaction solution is extracted with diethyl ether
  10. extractionextraction with diethyl ether
  11. dry with materialthe combined ether phases are dried
  12. customevaporated

Sources & evidence

ORD record
ord-c44ff154f4b14c3db056570dcd02fc88
Source dataset
uspto-grants-1980_12
Patent number
US04239901

Reaction notes

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