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Triethylamine → N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamide

HRID 541829
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 541829
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[Cl:23][C:24]1[N:29]=[C:28](Cl)[C:27]([Cl:31])=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>CN(C=O)C>[Cl:23][C:24]1[N:29]=[C:28]([NH:1][C:2]2[CH:3]=[C:4]([NH:8][S:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=2)[C:27]([Cl:31])=[CH:26][N:25]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 66881065N-(3-Aminophenyl)-1-(3-nitrophenyl)methanesulfonamide Hydrochloride

Produkt 1

HCID 86636268N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamideAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(3-aminophenyl)-1-(3-nitrophenyl)methanesulfonamide-hydrogen chloride (0.10 g, 0.29 mmol) and 2,4,5-trichloropyrimidine (0.065 g, 0.35 mmol) in DMF (1 mL) was added potassium carbonate (0.20 g, 1.4 mmol). The resulting mixture was stirred overnight at room temperature. Additional triethylamine (0.099 mL, 0.71 mmol) was added and stirred again overnight. The reaction was then quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous phase was extracted with EtOAc. The combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated. The crude was purified by column chromatography to give the desired product (0.080 g, 60%). LCMS for C17H13Cl2N5O4S (M+H)+: m/z=453.9, 455.9.

Aufarbeitung

  1. stirringstirred again overnight
  2. customThe reaction was then quenched with sat'd NH4Cl and water
  3. additionEtOAc was added
  4. customthe layers separated
  5. extractionThe aqueous phase was extracted with EtOAc
  6. washThe combined organics were washed with water and brine
  7. dry with materialthen dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0b20f03c7f0c4902ba47c684a3307e39
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08871753B2

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