Benzoic acid, 3-sulfo- → 3-(2-Methyl-propane-1-sulfonyl)-benzoic acid

HRID 349761

Reaktionsgleichung

Reaktionsgleichung von HRID 349761
[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])([OH:4])(=[O:3])=O.C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH:21]([CH3:23])[CH3:22]>CC(N(C)C)=O>[CH3:20][CH:21]([CH3:23])[CH2:22][S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:3])=[O:4]

Komponenten

5

Edukt 3

HCID 8477Benzoic acid, 3-sulfo-HCID 10556Isobutyl iodideHCID 11430Potassium Carbonate

Produkt 1

HCID 223974593-(2-Methyl-propane-1-sulfonyl)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a suspension of 3-sulfo-benzoic acid (1 g) and potassium carbonate (1.2 g) in dimethylacetamide (10 ml) was added iso-butyl iodide (0.65 ml). The mixture was heated by microwaves (600W) at 150° C. for 15 minutes. The reaction mixture was partitioned between water (100 ml) and ethyl acetate (100 ml), the aqueous layer was separated, acidified to pH 1 with HCl (2N) and extracted with ethyl acetate (100 ml). The extract was evaporated to leave a residue which was purified by flash chromatography (Biotage 12S eluting with ethyl acetate:hexane:acetic acid, 29:70:1) to give the title product as a white solid (0.34 g).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water (100 ml) and ethyl acetate (100 ml)
  2. customthe aqueous layer was separated
  3. extractionextracted with ethyl acetate (100 ml)
  4. customThe extract was evaporated
  5. customto leave a residue which
  6. customwas purified by flash chromatography (Biotage 12S eluting with ethyl acetate:hexane:acetic acid, 29:70:1)

Quellen und Nachweise

ORD-Eintrag
ord-6839d0a7bf894358b55c5a2100b16021
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179922B2

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