Pyridine → HCID 86585634, compound

HRID 2376703Notes

Reaction equation

HRID 2376703 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 to −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 purity was isolated. F-NMR: −30.05 ppm (CClF2), −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-8945f2ef0a634eaa8b73d61efe6b445a
Source dataset
uspto-grants-2008_12
Patent number
US07468381B2

Reaction notes

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