Chlorine → HCID 10947501, compound

HRID 1532568Notes

Reaction equation

HRID 1532568 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]([CH3:18])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:19]Cl>C(O)(=O)C>[Cl:1][C:2]1[C:3]([C:9]2[C:13]([Cl:19])=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]([CH3:18])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 11044647HCID 11044647, compound

Product 1

HCID 10947501HCID 10947501, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.0 g of 3-(3,5-dichloro-2-pyridyl)-5-trifluoromethyl-1-methyl-[1H]-pyrazole (Example H12) are initially introduced into glacial acetic acid at 40° C., and chlorine gas is passed slowly over the solution, while stirring. The reaction can be monitored analytically by means of thin layer chromatography (silica gel 60 F254, eluting agent: n-hexane/ethyl acetate 4/1, UV). When no further starting material can be detected, the glacial acetic acid is removed in vacuo and the residue is partitioned between dilute aqueous sodium hydroxide solution and ethyl acetate. After extraction by shaking, the organic phase which has been separated off is washed with brine, dried over sodium sulfate, filtered and concentrated. The yellow oil is purified by means of flash chromatography (silica gel, eluting agent: n-hexane/ethyl acetate 5/1). 1.6 g of the desired compound are obtained as a yellow oil (70% of theory).

Workup

  1. customThe reaction
  2. washcan be monitored analytically by means of thin layer chromatography (silica gel 60 F254, eluting agent: n-hexane/ethyl acetate 4/1, UV)
  3. customthe glacial acetic acid is removed in vacuo
  4. customthe residue is partitioned between dilute aqueous sodium hydroxide solution and ethyl acetate
  5. extractionAfter extraction
  6. stirringby shaking
  7. customthe organic phase which has been separated off
  8. washis washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe yellow oil is purified by means of flash chromatography (silica gel, eluting agent: n-hexane/ethyl acetate 5/1)

Sources & evidence

ORD record
ord-f150bcca528743458997115c1076d802
Source dataset
uspto-grants-2001_03
Patent number
US06204221B1

Reaction notes

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