Aniline → 5-BROMO-N-PHENYLNICOTINAMIDE

HRID 340431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340431
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[Br:30][C:31]1[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=1)[C:36](O)=[O:37].[Cl-].[NH4+]>C(OCC)(=O)C.CN(C=O)C.O>[Br:30][C:31]1[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=1)[C:36]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:37]

Komponenten

9

Edukt 5

HCID 6115AnilineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 887075-Bromonicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 42730445-BROMO-N-PHENYLNICOTINAMIDE

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Aniline (99 μl), WSC.HCl (209 mg), and HOBt.H2O (167 mg) were added to a DMF (5 ml) solution containing 5-bromonicotinic acid (200 mg), followed by stirring at room temperature for 3 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. Diisopropylether and hexane were added to the obtained residue, solid matter was collected by filtration, and a white solid of 5-bromo-N-phenylnicotinamide (268 mg) was thus obtained.

Aufarbeitung

  1. customThe organic layer was collected
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. additionDiisopropylether and hexane were added to the obtained residue, solid matter
  6. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0eede96c938d4653a20e0ff78e84d3df
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895585B2

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