m-Chloroperbenzoic acid → HCID 22618454, compound

HRID 861256Notes

Reaction equation

HRID 861256 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[C:3]=1[S:23][CH3:24].ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl.ClCCl>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]([F:21])([F:20])[F:22])[C:3]=1[S:23]([CH3:24])=[O:33]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22618553HCID 22618553, compound

Product 1

HCID 22618454HCID 22618454, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthio-3-trifluoromethylpyrazole (1.0 g) in chloroform (40 ml) was treated with m-chloroperbenzoic acid (0.42 g), portionwise at room temperature. After stirring for 6 hours, the solution was diluted with dichloromethane and washed in turn with sodium sulphite solution, sodium hydroxide solution, and water. The solution was dried over anhydrous magnesium sulphate, and evaporated in vacuo to give a yellow oil. Purification by chromatography on silica (Merck, 200-400 mesh, 0.7 kg cm-2) eluting with dichloromethane-ethylacetate (4:1) gave 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylsulphinyl-3-trifluoromethylpyrazole in the form of a white solid, m.p. 142°-145° C. with decomposition.

Workup

  1. washwashed in turn with sodium sulphite solution, sodium hydroxide solution, and water
  2. dry with materialThe solution was dried over anhydrous magnesium sulphate
  3. customevaporated in vacuo
  4. customto give a yellow oil
  5. customPurification by chromatography on silica (Merck, 200-400 mesh, 0.7 kg cm-2)
  6. washeluting with dichloromethane-ethylacetate (4:1)

Sources & evidence

ORD record
ord-848ffb8487f14cd980348c774556f13f
Source dataset
uspto-grants-1998_02
Patent number
US05714191

Reaction notes

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