Methanesulfenyl chloride, trifluoro- → HCID 22591644, compound

HRID 22866

Reaction equation

HRID 22866 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]([NH:18][CH2:19][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)=[CH:16][CH:15]=[N:14]1.[F:26][C:27]([F:31])([F:30])[S:28]Cl.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([NH:18][CH2:19][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)=[C:16]([S:28][C:27]([F:31])([F:30])[F:26])[CH:15]=[N:14]1

Participants

5

Reactant 3

HCID 67900Methanesulfenyl chloride, trifluoro-HCID 516892Sodium BicarbonateHCID 22591646HCID 22591646, compound

Product 1

HCID 22591644HCID 22591644, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.0 g of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(pyrazin-2-ylmethylamino)pyrazole dissolved in 30 ml of dried methylene chloride under a nitrogen atmosphere was added 14 ml of dried methylene chloride solution of trifluoromethylsulfenyl chloride at room temperature over about 1 hour, followed by stirring overnight. Saturated aqueous sodium hydrogen carbonate solution was added thereto, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and water several times. Thereafter, the layer was purified by a silica gel column chromatography. After removal of solvent, drying in vacuo afforded 3.59 g of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfenyl-5-(pyrazin-2-ylmethylamino)pyrazole.

Workup

  1. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and water several times
  2. customThereafter, the layer was purified by a silica gel column chromatography
  3. customAfter removal of solvent
  4. customdrying in vacuo

Sources & evidence

ORD record
ord-bd89ebcad29448aa87d9d887ef9be4bb
Source dataset
uspto-grants-2005_02
Patent number
US06849633B2

Linked notes

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