Sodium Hydroxide → 3-(Methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid

HRID 2071119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2071119
[CH3:1][N:2]([C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14]C)=[O:13])[S:3]([CH3:6])(=[O:5])=[O:4].[OH-].[Na+]>C1COCC1.CO.O>[CH3:20][O:19][C:17]([C:9]1[CH:10]=[C:11]([CH:16]=[C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])[CH:8]=1)[C:12]([OH:14])=[O:13])=[O:18]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 11324067Dimethyl 5-(N-methylmethylsulfonamido)isophthalate

Produkt 1

HCID 111503713-(Methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acidAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

Dimethyl 5-(N-methylmethylsulfonamido)isophthalate (0.842 g, 2.8 mmol) was dissolved in THF:MeOH (1:1) (8 mL) and H2O (3 mL). Solid NaOH (0.112 g, 2.8 mmol) was added and stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure. Saturated NaHCO3 (10 mL) was added to the reaction mixture and extracted with toluene (to remove <10% unreacted starting material). The aqueous solution was acidified with dilute HCl (10%), extracted with EtOAc, and dried over anhydrous Na2SO4. The solvent was evaporated and dried under reduced pressure to give 3-(methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid as a white solid (75%, 0.598 g), which was used without further purification.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionSaturated NaHCO3 (10 mL) was added to the reaction mixture
  3. extractionextracted with toluene (to remove <10% unreacted starting material)
  4. extractionextracted with EtOAc
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was evaporated
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-65840668ed584f76ab0e7955ecb0ed9f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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