4-Hydroxybenzaldehyde → HCID 178482857, Verbindung

HRID 527256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527256
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[C:3]=1[C:17]([NH2:19])=[O:18].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.N1CCCCC1>C(O)C>[CH3:16][N:14]([CH3:15])[C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:4]2[C:3]([C:17]([NH2:19])=[O:18])=[C:2]([N:1]=[CH:25][C:24]3[CH:27]=[CH:28][C:21]([OH:20])=[CH:22][CH:23]=3)[NH:6][N:5]=2)=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 8082PiperidineHCID 867018655-amino-3-((4-(dimethylamino)phenyl)amino)-1H-pyrazole-4-carboxamide

Produkt 1

HCID 178482857HCID 178482857, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

5-amino-3-((4-(dimethylamino)phenyl)amino)-1H-pyrazole-4-carboxamide (900 mg) was suspended in 10 mL of ethanol and 4-hydroxybenzaldehyde (634 mg, 1.5 eq.) and piperidine (0.25 eq., 89 mL) was added. The reaction was stirred at reflux until the starting material was absent and confirmed by HPLC. After the reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain 3-((4-(dimethylamino)phenyl)amino)-5-((4-hydroxybenzylidene)amino)-1H-pyrazole-4-carboxamide t as a yellow to orange powder. The product was washed with ethanol to remove any excess 4-hydroxybenzaldehyde. Product was allowed to dry under vacuum for 1 hr (1.130 g, 90% yield).

Aufarbeitung

  1. temperatureat reflux until the starting material
  2. custom(18 hrs) it
  3. customwas brought to room temperature
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-604c007cda2a4dacb6578cb178a72b4b
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346792B2

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