Phosphorus pentachloride → HCID 22267925, compound

HRID 2298024Notes

Reaction equation

HRID 2298024 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[C:13]([S:15](O)(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=3[Cl:19])[N:7]=[CH:6][C:5]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)(Cl)[Cl:26]>O=P(Cl)(Cl)Cl>[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[C:13]([S:15]([Cl:26])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=3[Cl:19])[N:7]=[CH:6][C:5]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 22267748HCID 22267748, compound

Product 1

HCID 22267925HCID 22267925, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of ethyl 5-cyclopropyl-1-(2-chloro-5-{hydroxysulfonyl}phenyl)-1H-pyrazole-4-carboxylate (1.48 g, 4.0 mmol) and PCl5 (1.79 g, 8.6 mmol) in POCl3 (6 mL) under a nitrogen atmosphere was heated at 95° C. for 30 min, cooled to 23° C. and poured slowly over ice. The resulting mixture was extracted with EtOAc. The organic layer was washed three times with cold water, brine, dried over MgSO4, filtered and concentrated in vacuo to afford 1.48 g (95% yield) of ethyl 5-cyclopropyl-1-(2-chloro-5-{chlorosulfonyl}phenyl)-1H-pyrazole-4-carboxylate as a yellow oil.

Workup

  1. temperaturecooled to 23° C.
  2. additionpoured slowly over ice
  3. extractionThe resulting mixture was extracted with EtOAc
  4. washThe organic layer was washed three times with cold water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1ecb19ed19c4f6cb49ab39f45d0ce9d
Source dataset
uspto-grants-2002_12
Patent number
US06492401B1

Reaction notes

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