Benzenesulfonamide → Benzamide, 2,4,5-trifluoro-N-(phenylsulfonyl)-

HRID 2359311Notes

Reaction equation

HRID 2359311 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:13]1([S:19]([NH2:22])(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH:22][S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20])=[O:6]

Participants

5

Reactant 2

HCID 7370BenzenesulfonamideHCID 5211702,4,5-Trifluorobenzoic acid

Product 1

HCID 58046338Benzamide, 2,4,5-trifluoro-N-(phenylsulfonyl)-Yield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4,5-trifluorobenzoic acid (0.50 g, 2.8 mmol) in dichloromethane (5 mL) was added N-di-isopropylethylamine (1.8 mL, 1.3 g, 8.5 mmol), WSCDI (0.82 g, 4.2 mmol) and DMAP (0.52 g, 4.2 mmol). After 10 minutes phenylsulfonamide (0.45 g, 4.2 mmol) was added and the reaction left at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue purified by reverse phase chromatography using CH3CN/water as eluent (5:95-95/5 over 30 mins) to yield the title compound (0.60 g, 67%) as a white solid

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by reverse phase chromatography
  3. custom(5:95-95/5 over 30 mins)

Sources & evidence

ORD record
ord-2ca7feea9c48460daf0c7d9824cec811
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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