4-chloro-N-[2-(2-chloro-5-nitro-benzoyl)-5-methyl-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide → N-[2-(5-amino-2-chloro-benzoyl)-5-methyl-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzenesulfonamide

HRID 1898181Notes

Reaction equation

HRID 1898181 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19](=[O:30])[C:20]3[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:21]=3[Cl:29])=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32]>CC(O)=O.CCOC(C)=O.[Fe]>[NH2:26][C:24]1[CH:23]=[CH:22][C:21]([Cl:29])=[C:20]([CH:25]=1)[C:19]([C:13]1[C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:31]([F:34])([F:33])[F:32])[CH:4]=2)(=[O:10])=[O:9])=[CH:17][C:16]([CH3:18])=[CH:15][N:14]=1)=[O:30]

Participants

5

Reactant 1

HCID 579424904-chloro-N-[2-(2-chloro-5-nitro-benzoyl)-5-methyl-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 57942517N-[2-(5-amino-2-chloro-benzoyl)-5-methyl-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzenesulfonamideYield 92.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To Fe powder (61.3 mg, 1.09 mmol), AcOH (2 mL) was added dropwise and heated to 80° C. To it, a solution of 4-chloro-N-[2-(2-chloro-5-nitro-benzoyl)-5-methyl-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (136 mg, 0.255 mmol) in AcOH (2 mL) was added slowly. After 30 min, reaction mixture was allowed to cool to room temperature and diluted with EtOAc (25 mL), filtered through a pad of Celite. The filter cake was washed with EtOAc (25 mL) and the filtrate was concentrated. The residual liquid was slowly treated with saturated aqueous NaHCO3 solution, followed by small portions of solid NaHCO3 to neutralize the AcOH, extracted with EtOAc (2×25 mL) and the extracts were dried (anhydrous Na2SO4), concentrated under reduced pressure and purified (SiO2, EtOAc) to get N-[2-(5-amino-2-chloro-benzoyl)-5-methyl-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzenesulfonamide (118 mg) in 92.2% yield. ESMS m/z (relative intensity): 504 (M+H)+ (100).

Workup

  1. customreaction mixture
  2. temperatureto cool to room temperature
  3. filtrationfiltered through a pad of Celite
  4. washThe filter cake was washed with EtOAc (25 mL)
  5. concentrationthe filtrate was concentrated
  6. additionThe residual liquid was slowly treated with saturated aqueous NaHCO3 solution
  7. extractionextracted with EtOAc (2×25 mL)
  8. dry with materialthe extracts were dried (anhydrous Na2SO4)
  9. concentrationconcentrated under reduced pressure
  10. custompurified (SiO2, EtOAc)

Sources & evidence

ORD record
ord-54f4c529bd8848cfb894adfb5e355525
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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