Acetic Acid → HCID 10947501, compound

HRID 650483Notes

Reaction equation

HRID 650483 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.C(O)(=O)C.[Cl:23]Cl>CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:9]2[C:13]([Cl:23])=[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

5

Reactant 3

HCID 176Acetic AcidHCID 24526ChlorineHCID 11044647HCID 11044647, compound

Product 1

HCID 10947501HCID 10947501, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

2.0 g of 3-(3,5-dichloro-2-pyridyl)-5-trifluoromethyl-1-methyl-[1H]-pyrazole (Example P11) are introduced into glacial acetic acid at 40° C. and, with stirring, chlorine gas is slowly passed over the solution. The reaction can be monitored analytically by means of thin-layer chromatography (silica gel 60 F254, eluant: n-hexanelethyl acetate 4/1, UV). Once starting material can no longer be detected, 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 separated organic phase is washed with brine, dried over sodium sulfate, filtered and concentrated. The yellow oil is purified by means of flash chromatography (silica gel; eluant: n-hexane/ethyl acetate 5/1). 1.6 g of of the desired compound are obtained in the form of a yellow oil (70% of the theoretical yield).

Workup

  1. customThe reaction
  2. customglacial acetic acid is removed in vacuo
  3. customthe residue is partitioned between dilute aqueous sodium hydroxide solution and ethyl acetate
  4. extractionAfter extraction
  5. stirringby shaking
  6. washthe separated organic phase is washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe yellow oil is purified by means of flash chromatography (silica gel; eluant: n-hexane/ethyl acetate 5/1)

Sources & evidence

ORD record
ord-06a973a363444682a4ab7ded172fe2cd
Source dataset
uspto-grants-2001_08
Patent number
US06274536B1

Reaction notes

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