Water → 4-Bromo-2-(methylsulfonamido)benzoic acid

HRID 2411352Notes

Reaction equation

HRID 2411352 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>O1CCCC1>[Br:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 17871390Methyl 2-Amino-4-bromobenzoate

Product 1

HCID 226210824-Bromo-2-(methylsulfonamido)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-amino-4-bromobenzoate (1 g) was dissolved in tetrahydrofuran (15 mL), triethylamine (4.2 mL) and methanesulfonyl chloride (0.74 mL) were added, and the mixture was stirred at room temperature for 6 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. After evaporation of the solvent, to the residue were added methanol (20 mL) and 1N aqueous sodium hydroxide solution (13 mL), and the mixture was stirred at 50-60° C. After neutralizing with 1N hydrochloric acid, the precipitated solid was collected by filtration to give the title compound (964 mg).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customAfter evaporation of the solvent
  3. additionto the residue were added methanol (20 mL) and 1N aqueous sodium hydroxide solution (13 mL)
  4. stirringthe mixture was stirred at 50-60° C
  5. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-9508b847c23b401ea2a18cf38e45e780
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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