Dimethyl acetylsuccinate → HCID 178499519, Verbindung

HRID 472809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472809
[C:1]1([C:7]2[CH:11]=[C:10]([NH2:12])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([CH:16]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:17](OC)=[O:18])(=O)[CH3:14]>C1(C)C(C)=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:14][C:13]1[NH:12][C:10]2[N:9]([N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=2)[C:17](=[O:18])[C:16]=1[CH2:21][C:22]([O:24][CH3:25])=[O:23]

Komponenten

5

Edukt 2

HCID 112039Dimethyl acetylsuccinateHCID 1366553-Amino-5-phenylpyrazole

Produkt 1

HCID 178499519HCID 178499519, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

To a solution of 3-phenyl-1H-pyrazol-5-amine (4 g, 25.1 mmol) and dimethyl 2-acetylsuccinate (12 mL, 74.0 mmol) in xylene (120 mL) was added p-toluenesulfonic acid monohydrate (50 mg, 0.263 mmol). The reaction mixture was heated at reflux under a Dean-Stark trap for 20 h. The solid was filtered and washed with hexanes to afford the title compound (6.4 g, 86%). 1H-NMR (400 MHz, MeOD) δ ppm 2.37 (3H, s), 3.66 (2H, s), 3.72 (3H, s), 6.46 (1H, s), 7.34-7.53 (3H, m), 7.87-8.06 (2H, m).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a Dean-Stark trap for 20 h
  3. filtrationThe solid was filtered
  4. washwashed with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4d883600fa2a4fe3a7faa7cd0d16926f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633200B2

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