Pyridine → HCID 22252930, compound

HRID 413754Notes

Reaction equation

HRID 413754 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([OH:18])=[C:16]([S:19][C:20]([F:23])([F:22])[F:21])[C:15]([C:24]#[N:25])=[N:14]1.N1C=CC=CC=1.[CH3:32][C:33]([CH3:38])([CH3:37])[C:34](Cl)=[O:35]>ClCCCl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([O:18][C:34](=[O:35])[C:33]([CH3:38])([CH3:37])[CH3:32])=[C:16]([S:19][C:20]([F:23])([F:21])[F:22])[C:15]([C:24]#[N:25])=[N:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 178510673HCID 178510673, compound

Product 1

HCID 22252930HCID 22252930, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To the solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfenyl-5-hydroxypyrazole (7.00 g, 16.6 mmol) and pyridine (4.91 g, 62.1 mmol) in 1,2-dichloroethane at room temperature was added trimethylacetyl chloride (4.37 g, 36.2 mmol) dropwise. Ice bath was used to maintain the temperature of the reaction. After 20 hr at room temperature, the orgainc layer was washed with five times of aqueous KHS04 till the aqueous solution was at pH 1. The orgainc layer was then dried (Mg SO4) and concentrated to give a solid residue. Upon chromatographic purification via silica gel column of the solid residue, after trituration with pentane, a off white solid (2.403 g, 28.6% yield, 97.0% HPLC puriety) was provided as the desired product, m. p. 82-83 C.

Workup

  1. customIce bath was used
  2. temperatureto maintain
  3. customthe temperature of the reaction
  4. washthe orgainc layer was washed with five times of aqueous KHS04 till the aqueous solution
  5. dry with materialThe orgainc layer was then dried (Mg SO4)
  6. concentrationconcentrated
  7. customto give a solid residue
  8. customUpon chromatographic purification via silica gel column of the solid residue

Sources & evidence

ORD record
ord-dac991a22aeb4bb88d2297fdd3fd5941
Source dataset
uspto-grants-2003_05
Patent number
US06569886B2

Reaction notes

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