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m-Bromobenzenesulphonyl chloride → HCID 57751032, Verbindung

HRID 2283287
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2283287
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([NH2:22])(=[O:21])=[O:20]>N1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([NH2:22])(=[O:20])=[O:21])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 17943m-Bromobenzenesulphonyl chlorideHCID 728942-Aminobenzenesulfonamide

Produkt 1

HCID 57751032HCID 57751032, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-Bromo-benzenesulfonyl chloride (8.34 mL, 57.9 mmol) was added to a solution of 2-amino-benzenesulfonamide (9.965 g, 57.9 mmol) dissolved in pyridine (90 mL). The reaction was stirred for 4 h followed by solvent removal under vacuo. The reaction mixture was added to water and the product was extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated to furnish a dark yellow oil. The oil was dissolved in EtOAc and precipitated by addition of heptane. The solid was finally recrystallized from EtOH to give the title compound (10.784 g, 48%) as a white solid.

Aufarbeitung

  1. customfollowed by solvent removal under vacuo
  2. additionThe reaction mixture was added to water
  3. extractionthe product was extracted three times with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto furnish a dark yellow oil
  9. customprecipitated by addition of heptane
  10. customThe solid was finally recrystallized from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-41af0ff7580945f4af61d1bc4095ccac
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09145380B2

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