Sulfuric Acid → 3-Isobutylamino-2-methyl-4-(methylsulfonyl)benzoic acid

HRID 547247Notes

Reaction equation

HRID 547247 reaction equation
F[C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([OH:7])=[O:6].[CH2:16]([NH2:20])[CH:17]([CH3:19])[CH3:18].S(=O)(=O)(O)O>>[CH2:16]([NH:20][C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])[C:5]([OH:7])=[O:6])[CH:17]([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6558IsobutylamineHCID 142544793-Fluoro-2-methyl-4-(methylsulfonyl)benzoic acid

Product 1

HCID 574365663-Isobutylamino-2-methyl-4-(methylsulfonyl)benzoic acid

Procedure

2.0 g (9 mmol) of 3-fluoro-2-methyl-4-(methylsulfonyl)benzoic acid were dissolved in 26.5 ml (267 mmol) of isobutylamine. The mixture was heated at reflux with stirring for 8 days, cooled to RT, acidified with 10% strength sulfuric acid and extracted twice with ethyl acetate. The combined organic phases were dried over MgSO4, and the solvent was removed under reduced pressure. This gave 2.4 g of a colorless solid of a purity of 98%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d0da8512be5e44a8bb6f2c4e224bc5ff
Source dataset
uspto-grants-2011_05
Patent number
US07939467B2

Reaction notes

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