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

HRID 548526Notes

Reaction equation

HRID 548526 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]([NH2:19])[CH:17]=[CH2:18].S(=O)(=O)(O)O>O>[CH2:16]([NH:19][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]=[CH2:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7853Allylamine2×HCID 142544793-Fluoro-2-methyl-4-(methylsulfonyl)benzoic acid

Product 1

HCID 574249463-Allylamino-2-methyl-4-(methylsulfonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.0 g (17 mmol) of 3-fluoro-2-methyl-4-(methylsulfonyl)benzoic acid were dissolved in 12.9 ml (172 mmol) of allylamine. The mixture was heated at reflux for 5 days and allowed to stand for 2 days. 10 ml (134 mmol) of allylamine and 15 ml of water were added, and the mixture was heated at reflux for 14 days, cooled to RT, added to ice, 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. The residue was crystallized from diethyl ether. This gave 4.2 g of a yellow solid of a purity of 88%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 days
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 14 days
  5. additionadded to ice
  6. extractionextracted twice with ethyl acetate
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-f2d7b7f3e63b4a9fbed943a20408ee9e
Source dataset
uspto-grants-2011_05
Patent number
US07943550B2

Reaction notes

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