Water → HCID 86647608, compound

HRID 1256587Notes

Reaction equation

HRID 1256587 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:22])[C:9]=2SC)=[CH:4][CH:3]=1.Cl[C:33]1C=CC=C(C(OO)=O)C=1.O.ClC1C=CC(C2N(C3C=CC(Cl)=CC=3Cl)N=C(C(NN3CCCCC3)=O)C=2[S:73](C)=[O:74])=CC=1>ClCCl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][C:29]3=[S:73]=[O:74])=[O:22])[C:9]=2[CH3:33])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 23624319HCID 23624319, compoundHCID 24863732HCID 24863732, compound

Product 1

HCID 86647608HCID 86647608, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a magnetically stirred solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylsulfanyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide (0.70 gram, 1.41 mmol) was added m-chloro-perbenzoic acid (m-CPBA) (0.50 gram of a 70% aqueous solution, 2.0 mmol). The resulting mixture was reacted for 20 hours at room temperature and subsequently poured into water (25 ml). The resulting mixture was extracted with dichloromethane (25 ml). The organic layer was separated and dried over MgSO4, filtered and concentrated. Column chromatography (silica gel, dichloromethane/methanol=95/5 (v/v)) gave 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-sulfinyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide (150 mg, 21% yield) (compound 5).

Workup

  1. customThe resulting mixture was reacted for 20 hours at room temperature
  2. extractionThe resulting mixture was extracted with dichloromethane (25 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-52879a6860da4ccfa35e1fed6f931e76
Source dataset
uspto-grants-2013_06
Patent number
US08461184B2

Reaction notes

Loading…