Hydrochloric Acid → 5-Bromo-pyridine-2-carboxylic acid (4-chloro-phenyl)-amide

HRID 1754668

Reaktionsgleichung

Reaktionsgleichung von HRID 1754668
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](Cl)=[O:9])=[N:6][CH:7]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.N1C=CC=CC=1.Cl>C(#N)C.CN(C)C1C=CN=CC=1.O>[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[O:9])=[CH:14][CH:13]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 78124-ChloroanilineHCID 190907715-Bromo-pyridine-2-carbonyl chloride

Produkt 1

HCID 595933715-Bromo-pyridine-2-carboxylic acid (4-chloro-phenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
68 °C

Versuchsvorschrift

To 5-Bromo-pyridine-2-carbonyl chloride (69, 0.76 g, 3.4 mmol) in acetonitrile (29.0 mL) were added p-chloroaniline (53, 0.702 g, 5.50 mmol), 4-dimethylamino-pyridine (0.12 g, 0.96 mmol) and pyridine (2.9 mL, 0.036 mol). The reaction was stirred at 68° C. overnight, then poured into water, acidified with 1 N HCl to pH around 1 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with dichloromethane to give a white solid (70, 0.75 g, 70.0%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with dichloromethane
  7. customto give a white solid (70, 0.75 g, 70.0%)

Quellen und Nachweise

ORD-Eintrag
ord-8e008afd859e4f64af1769cc35c5488f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169250B2

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