Diethyl Ether → 5-[5-(4-bromophenyl)-4-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinesulfonamide

HRID 394861Notes

Reaction equation

HRID 394861 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[N:17][CH:18]=3)[N:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)=[CH:4][CH:3]=1.[Cl:27]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(OCC)C>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:20])=[O:21])=[N:17][CH:18]=3)[N:11]=[C:10]([C:23]([F:26])([F:24])[F:25])[C:9]=2[Cl:27])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24477Sodium ThiosulfateHCID 31398Chlorosuccinimide2×HCID 129686175-[5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinesulfonamide

Product 1

HCID 223138055-[5-(4-bromophenyl)-4-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinesulfonamideYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinesulfonamide (350 mg, 0.783 mmol) in N,N-dimethylformamide (12 ml) was added N-chlorosuccinimide (1.05 g, 7.83 mmol) at room temperature. After the mixture was stirred for 18 hr, 1.05 g of N-chlorosuccinimide was added. The resulting mixture was stirred for further 36 hr. 20 ml of saturated aqueous sodium thiosulfate and 50 ml of diethyl ether were added and the two-phase-mixture was stirred for 0.5 hr. The separated organic layer was washed with water (20 ml×3) and dried over magnesium sulfate. Removal of solvent gave a pale yellow gum, which was chromatographed on a column of silica gel (50 g) eluting with ethyl acetate/hexane (1:3) to afford 236 mg (63%) of the title compound as a white solid.

Workup

  1. stirringThe resulting mixture was stirred for further 36 hr
  2. stirringthe two-phase-mixture was stirred for 0.5 hr
  3. washThe separated organic layer was washed with water (20 ml×3)
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of solvent
  6. customgave a pale yellow gum, which
  7. customwas chromatographed on a column of silica gel (50 g)
  8. washeluting with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-086ee2dbd309416896d9a2cff6cfea6c
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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