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

HRID 651074Notes

Reaction equation

HRID 651074 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-2915342031d34f78ac52c174fc35b8ec
Source dataset
uspto-grants-2001_08
Patent number
US06277885B1

Reaction notes

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