Pyridine → HCID 22252930, compound

HRID 2376702Notes

Reaction equation

HRID 2376702 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 organic layer was washed five times with aqueous KHSO4 till the aqueous solution was at pH 1. The organic layer was then dried (MgSO4) 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 purity) 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 organic layer was washed five times with aqueous KHSO4 till the aqueous solution
  5. dry with materialThe organic layer was then dried (MgSO4)
  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-264df5cbd9184145ae062b2c5ea07cf2
Source dataset
uspto-grants-2008_12
Patent number
US07468381B2

Reaction notes

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