Maleic Anhydride → 4-(2,5-Dioxo-2,5-dihydro-1h-pyrrol-1-yl)-2-(trifluoromethyl)benzonitrile

HRID 723684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723684
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]#[N:11])[NH2:6].[C:14]1(=O)[O:19][C:17](=[O:18])[CH:16]=[CH:15]1>C(O)(=O)C>[O:18]=[C:17]1[CH:16]=[CH:15][C:14](=[O:19])[N:6]1[C:5]1[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=1

Komponenten

4

Edukt 2

HCID 7923Maleic AnhydrideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

Produkt 1

HCID 218749284-(2,5-Dioxo-2,5-dihydro-1h-pyrrol-1-yl)-2-(trifluoromethyl)benzonitrileAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A mixture of 3-trifluoromethyl-4-cyano-aniline (24.0 g, 129 mmol) and maleic anhydride (14.0 g, 143 mmol) in 50 mL of acetic acid was heated at 115° C. overnight. A precipitate was obtained during the heating period. The reaction was allowed to stand at rt for an additional overnight period. The solid was removed by filtration, the filter cake was washed with diethyl ether and dried to give 21 g (79 mmol, 61%) of compound 471A as an off white solid. HPLC: 100% at 2.11 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10–90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Aufarbeitung

  1. customA precipitate was obtained during the heating period
  2. customThe solid was removed by filtration
  3. washthe filter cake was washed with diethyl ether
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-473d81588ba24b69b08a8da4073a86d0
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141578B2

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