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 419171Notes

Reaction equation

HRID 419171 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-02e529c32222422f9170535c61c1fdba
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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