Pyridine → HCID 86585634, compound

HRID 413755Notes

Reaction equation

HRID 413755 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])=[CH:16][C:15]([C:19]#[N:20])=[N:14]1.N1C=CC=CC=1.Cl[C:28]([F:32])([F:31])[S:29]Cl.[Cl:33]CCl>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([OH:18])=[C:16]([Cl:33])[CH:15]([C:19]#[N:20])[N:14]1[S:29][CH:28]([F:32])[F:31]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 12621923Chloro(chlorosulfanyl)difluoromethaneHCID 178510263HCID 178510263, compound

Product 1

HCID 86585634HCID 86585634, compoundYield 71%

Procedure

To the solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-hydroxypyrazole (12.0 g, 37.3 mmol.) and pyridine (3.25 g, 41.0 mmol) in dichloromethane at −50-−60 C. was added chlorodifluoromethanesulfenyl chloride (8.1 g, 46.6 mmol). The resulting solution was gradually warmed up to room temperature. After 20 hr, the organic layer was washed five times with water. It was then washed with brine and dried (Na2SO4) to provide an oil. Upon chromatographic purification of the oil , a total of 11.6 g (26.4 mmol., 71% yield) of the desired product with 97% HPLC puriety was isolated. F-NMR: −30.05 ppm (CCIF2), −63.80 ppm (ArCF3).

Workup

  1. washthe organic layer was washed five times with water
  2. washIt was then washed with brine
  3. dry with materialdried (Na2SO4)
  4. customto provide an oil
  5. customUpon chromatographic purification of the oil

Sources & evidence

ORD record
ord-60e0e5e3135b44b29cb26a870f4454ca
Source dataset
uspto-grants-2003_05
Patent number
US06569886B2

Reaction notes

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