4-Hydroxybenzaldehyde → HCID 178482857, Verbindung

HRID 1049159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1049159
[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 μL) 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-c3432c83dcf3481db99b982069c3d147
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382237B2

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