Sulfuric Acid → 3-(2,2-Diethoxyethyl)amino-2-methyl-4-(methylsulfonyl)benzoic acid

HRID 547249Notes

Reaction equation

HRID 547249 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]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][NH2:21])[CH3:17].OS(O)(=O)=O>>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][NH:21][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])[CH3:17]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 695242,2-DiethoxyethylamineHCID 142544793-Fluoro-2-methyl-4-(methylsulfonyl)benzoic acid

Product 1

HCID 671984093-(2,2-Diethoxyethyl)amino-2-methyl-4-(methylsulfonyl)benzoic acid

Conditions

Temperature
120 °C

Procedure

5.1 g (22 mmol) of 3-fluoro-2-methyl-4-(methylsulfonyl)benzoic acid were dissolved in 30 ml (218 mmol) of aminoacetaldehyde diethyl acetal. The mixture was heated at 120° C. with stirring for 2 days, cooled to RT, acidified with 10% strength H2SO4 and extracted twice with ethyl acetate. The combined organic phases were dried over MgSO4, and the solvent was removed under reduced pressure. This gave 4.0 g of a yellow oil of a purity of 91%.

Workup

  1. temperaturecooled to RT
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-89690ad9344d42e9a88f58b1e6e6c7a6
Source dataset
uspto-grants-2011_05
Patent number
US07939467B2

Reaction notes

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