Water → 3-Methyl-5-bromo-2-(4-fluoro-benzenesulfonylamino)-benzoic acid

HRID 1883531Notes

Reaction equation

HRID 1883531 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[NH2:12].[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>N1C=CC=CC=1>[CH3:11][C:6]1[C:5]([NH:12][S:21]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)(=[O:23])=[O:22])=[C:4]([CH:9]=[C:8]([Br:10])[CH:7]=1)[C:3]([OH:2])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 95884-Fluorobenzenesulfonyl chlorideHCID 2763413Methyl 2-amino-5-bromo-3-methylbenzoate

Product 1

HCID 215844933-Methyl-5-bromo-2-(4-fluoro-benzenesulfonylamino)-benzoic acidYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 25.0 g (0.102 mol) of 2-amino-3-methyl-5-bromobenzoic acid methyl ester (U.S. Pat. No. 5,776,961) in 300 mL of pyridine was added 21.93 g (0.113 mol) of 4-fluorobenzenesulfonyl chloride. The reaction mixture was stirred for 18 h at 80°, cooled to room temperature and poured into water. The resulting mixture was extracted with ethyl acetate and the combined organics were then washed with 5% HCl solution and water. The organic layer was then dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to provide 14.53 g (39%) of the desired product as a tan solid. Electrospray Mass Spec: 388.0 (M−H)−

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washthe combined organics were then washed with 5% HCl solution and water
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-989095f6fa1d467c9ee55125e96f22a1
Source dataset
uspto-grants-2004_07
Patent number
US06762178B2

Reaction notes

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