Dimethylamine → 2-amino-5-bromo-N,N-dimethylpyridine-3-sulfonamide

HRID 472096

Reaktionsgleichung

Reaktionsgleichung von HRID 472096
[NH2:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1.[N:13]1[CH:18]=CC=C[CH:14]=1.CNC.C1COCC1>O1CCOCC1>[NH2:1][C:2]1[C:7]([S:8]([N:13]([CH3:18])[CH3:14])(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 1049PyridineHCID 8028TetrahydrofuranHCID 533020262-Amino-5-bromopyridine-3-sulfonyl chloride

Produkt 1

HCID 523351532-amino-5-bromo-N,N-dimethylpyridine-3-sulfonamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a cold (0 C) suspension of 2-amino-5-bromo-3-pyridinesulfonyl chloride (92.1 mmol) in dry 1,4-dioxane (92 mL) was added pyridine (101.3 mmol) followed by a 2M solution of dimethylamine in THF (101.3 mmol). The reaction was allowed to warm to rt for 2 h, heated to 50 C for 1 h, then cooled to rt. After standing for 2 h, the precipitate was collected by filtration and rinsed with a minimal amount of cold water. Drying the precipitate to constant weight under high vacuum provided 14.1 g (55%) of the title compound as a white solid. MS (ES)+m/e 279.8, 282.0 [M+H]+.

Aufarbeitung

  1. temperatureheated to 50 C for 1 h
  2. temperaturecooled to rt
  3. filtrationthe precipitate was collected by filtration
  4. washrinsed with a minimal amount of cold water
  5. customDrying the precipitate to constant weight under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-897a678f2067438d831a0eadeb4346b3
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633187B2

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