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Tetrahydrofuran → 4-(5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-benzoic acid methyl ester

HRID 1790219
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1790219
C1COCC1.[NH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[S:17]([CH3:20])(=[O:19])=[O:18].[H-].[Na+].[Cl:23][C:24]1[CH:37]=[CH:36][C:27]2[S:28][C:29]([S:32](Cl)(=[O:34])=[O:33])=[C:30]([CH3:31])[C:26]=2[CH:25]=1>CN(C=O)C>[Cl:23][C:24]1[CH:37]=[CH:36][C:27]2[S:28][C:29]([S:32]([NH:6][C:7]3[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=3[S:17]([CH3:20])(=[O:19])=[O:18])(=[O:33])=[O:34])=[C:30]([CH3:31])[C:26]=2[CH:25]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydride2×HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 22041468methyl 4-Amino-3-methylsulfonylbenzoate

Produkt 1

HCID 101624624-(5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-benzoic acid methyl esterAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into a mixed solvent of 20 mL of THF and 3 mL of DMF was dissolved 985 mg of methyl 4-amino-3-methanesulfonylbenzoate, followed by addition of 170 mg of sodium hydride (oily, 60%) at 0° C. After 20 minutes of stirring at the same temperature, 1.28 g of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at 0° C., followed by 1 hour of stirring at room temperature. Further, 150 mg of sodium hydride (oily, 60%) was added at room temperature and the mixture was stirred for 2 hours at the same temperature. After confirmation of disappearance of the starting material, the reaction was terminated by adding saturated aqueous ammonium chloride solution at 0° C., followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1) to obtain 911 mg of the title compound as colorless powder.

Aufarbeitung

  1. additionwas added at 0° C.
  2. stirringthe mixture was stirred for 2 hours at the same temperature
  3. customAfter confirmation of disappearance of the starting material, the reaction was terminated
  4. additionby adding saturated aqueous ammonium chloride solution at 0° C.
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-c68c8c1c71e8490ca4bfbc32fb5643b0
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07071220B2

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