2-Aminobenzenesulfonamide → 2-(5-Bromo-2-chloropyrimidin-4-ylamino)benzenesulfonamide

HRID 2382635

Reaktionsgleichung

Reaktionsgleichung von HRID 2382635
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([NH2:20])(=[O:19])=[O:18].C(=O)([O-])O.[Na+]>CC(O)C.Cl>[Br:1][C:2]1[C:3]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([NH2:20])(=[O:18])=[O:19])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 728942-AminobenzenesulfonamideHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 859979922-(5-Bromo-2-chloropyrimidin-4-ylamino)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 5-bromo-2,4-dichloropyrimidine (300 mg, 1.32 mmol) and 2-amino-benzenesulfonamide (340 mg, 1.97 mmol) in 2-propanol (3 mL), concentrated hydrochloric acid (0.06 mL) is added and the mixture is stirred at 90° C. for 4.5 hours. The mixture is poured into aqueous sodium hydrogen carbonate and extracted with ethyl acetate three times. The organic layer is washed with water, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by column chromatography (hexane:ethyl acetate=2:1) to afford the title compound.

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue is purified by column chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-6cce7f7aba33426eaed060db6c035d52
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263590B2

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