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Tetrahydrofuran → HCID 12045135, Verbindung

HRID 1790220
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1790220
C1COCC1.[NH2:6][C:7]1[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:21])[CH:8]=1.[H-].[Na+].[Cl:24][C:25]1[CH:38]=[CH:37][C:28]2[S:29][C:30]([S:33](Cl)(=[O:35])=[O:34])=[C:31]([CH3:32])[C:27]=2[CH:26]=1>CN(C=O)C>[Cl:24][C:25]1[CH:38]=[CH:37][C:28]2[S:29][C:30]([S:33]([NH:6][C:7]3[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:21])[CH:8]=3)(=[O:34])=[O:35])=[C:31]([CH3:32])[C:27]=2[CH:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydride2×HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride2×HCID 10586307Methyl 4-amino-5-methanesulfonyl-2-methylbenzoate

Produkt 1

HCID 12045135HCID 12045135, VerbindungAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into 10 mL of THF was dissolved 135 mg of methyl 4-amino-5-methanesulfonyl-2-methylbenzoate, followed by addition of 22 mg of sodium hydride (oily, 60%) at room temperature. After 20 minutes of stirring at the same temperature, 130 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at 0° C., followed by 1 hour of stirring at room temperature and 5 hours of heating under refluxing. Further, 1 mL of DMF, 22 mg of sodium hydride (oily, 60%) and 50 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene were added and the mixture was heated under refluxing for 2.5 hours. 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=3/2) to obtain 102 mg of the title compound as colorless powder.

Aufarbeitung

  1. additionwas added at 0° C.
  2. temperatureof heating
  3. temperatureunder refluxing
  4. temperaturethe mixture was heated
  5. temperatureunder refluxing for 2.5 hours
  6. customAfter confirmation of disappearance of the starting material, the reaction was terminated
  7. additionby adding saturated aqueous ammonium chloride solution at 0° C.
  8. extractionfollowed by extraction with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed by evaporation
  12. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/2)

Quellen und Nachweise

ORD-Eintrag
ord-a152e2c19d984a5485caa2e2058b994e
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07071220B2

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