Ethyl Acetate → 5-Amino-1-(1-naphthyl)-3-(4-tolyl)pyrazole-4-carboxamide

HRID 582011

Reaktionsgleichung

Reaktionsgleichung von HRID 582011
[C:1]([C:3](=[C:7](SC)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[C:18]1([NH:28][NH2:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].C(OCC)(=O)C>CCCCCC>[NH2:2][C:1]1[N:28]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[N:29]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 519949Hydrazine, 1-naphthalenyl-, hydrochloride (1:1)HCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2×

Produkt 1

HCID 543553485-Amino-1-(1-naphthyl)-3-(4-tolyl)pyrazole-4-carboxamideAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl) acrylamide (464 mg, 2.0 mmol), 1-naphthyl hydrazine hydrochloride (389 mg, 2.0 mmol) and sodium hydroxide (88 mg, 2.2 mmol) following the procedure used for the compound of Example 12. The crude product was subjected to column chromatography (SiO2, 50-60% ethyl acetate in hexane) and was recrystallised from diethylether to give the title compound as pink crystals (185 mg) m.p. 195°. δH (CDCl3) 8.00 (1H, d, J 8.3 Hz), 7.95 (1 H., m), 7.73-7.55 (7H, m), 7.30 (2H, d, J 8.3 Hz), 5.52 (2H, br s), 5.16 (2H, br s) and 2.42 (3H, s).

Aufarbeitung

  1. customwas recrystallised from diethylether

Quellen und Nachweise

ORD-Eintrag
ord-ef930def809749ab9ca3e9e30e78bcdb
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922741

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