Methyl iodide → Dimethyl 5-(N-methylmethylsulfonamido)isophthalate

HRID 2071118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2071118
[H-].[Na+].[CH3:3][S:4]([NH:7][C:8]1[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:6])=[O:5].I[CH3:23]>CN(C=O)C>[CH3:23][N:7]([C:8]1[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])[S:4]([CH3:3])(=[O:6])=[O:5]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3711983Dimethyl 5-(methylsulfonamido)isophthalate

Produkt 1

HCID 11324067Dimethyl 5-(N-methylmethylsulfonamido)isophthalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred suspension of NaH (0.24 g, 10 mmol, 60% in oil dispersion) in 10 mL of DMF was added dimethyl 5-(methylsulfonamido)isophthalate (1.435 g, 5 mmol) followed by iodomethane (0.62 mL, 10 mmol) at room temperature. After 5 h, the reaction was quenched by H2O (25 mL). Then the reaction mixture was extracted with EtOAc, further washed with H2O to remove excess of DMF, dried over anhydrous Na2SO4 and concentrated. The crude product thus obtained was washed with hexanes to give dimethyl 5-(N-methylmethylsulfonamido)isophthalate as a white solid in 91% (1.37 g) yield.

Aufarbeitung

  1. customthe reaction was quenched by H2O (25 mL)
  2. extractionThen the reaction mixture was extracted with EtOAc
  3. washfurther washed with H2O
  4. customto remove excess of DMF
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe crude product thus obtained
  8. washwas washed with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8d7e507390404a2e8d7badc1f9135198
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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