Ethyl Acetate → 5-Amino-1-(2-tolyl)-3-(4-tolyl)pyrazole-4-carboxamide

HRID 582012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582012
[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([CH3:26])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][NH2:25].[OH-].[Na+].C(OCC)(=O)C>CCCCCC>[NH2:2][C:1]1[N:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH3:26])[N:25]=[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 71554o-Tolylhydrazinium(1+) chlorideHCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2×

Produkt 1

HCID 538751495-Amino-1-(2-tolyl)-3-(4-tolyl)pyrazole-4-carboxamideAusbeute 4,9 %

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), 2-tolylhydrazine hydrochloride (350 mg, 2.2 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, 75% ethyl acetate in hexane) to give the title compound as a yellow solid (30 mg) m.p. 133-135°. δH (CDCl3) 7.52 (2H, d, J 8.1 Hz), 7.38 (4H, m), 7.28 (2H, d, J 7.4 Hz), 5.40 (4H, m), 2.40 (3H, s) and 2.23 (3H, s).

Quellen und Nachweise

ORD-Eintrag
ord-d8cc42b5c4a14489adec7ee652103db8
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922741

Notizen zur Reaktion

Wird geladen…