4,5-Dichlorophthalic anhydride → (Z)-5,6-dichloro-3-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzylidene)isobenzofuran-1(3H)-one

HRID 1091748

Reaktionsgleichung

Reaktionsgleichung von HRID 1091748
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C:7](=O)[O:6][C:5]2=[O:13].[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]C(O)=O)=[CH:17][C:16]=1[C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:33][CH3:34])[CH2:29][CH2:28]1)=[O:26].C([O-])(=O)C.[Na+].[Al]>>[Cl:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[Cl:1])[C:5](=[O:13])[O:6]/[C:7]/2=[CH:21]\[C:18]1[CH:19]=[CH:20][C:15]([F:14])=[C:16]([C:25]([N:27]2[CH2:32][CH2:31][CH:30]([O:33][CH3:34])[CH2:29][CH2:28]2)=[O:26])[CH:17]=1

Komponenten

5

Edukt 4

HCID 703344,5-Dichlorophthalic anhydrideHCID 517045Sodium AcetateHCID 5359268AluminumHCID 577917632-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetic Acid

Produkt 1

HCID 57791853(Z)-5,6-dichloro-3-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzylidene)isobenzofuran-1(3H)-oneAusbeute 16,92 %

Reaktionsbedingungen

Temperatur
240 °C

Versuchsvorschrift

A flask charged with 5,6-dichloroisobenzofuran-1,3-dione (370 mg, 1.71 mmol), 2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetic acid (43) (496 mg, 1.68 mmol) and Sodium acetate (34 mg, 0.41 mmol) was lowered into a pre-heated aluminium block at 210° C. The resulting mixture was heated further and stirred at 240° C. for 1 hour then cooled. The residue was triturated, with sonication, under ethanol (˜25 mL) and solid collected by suction filtration to afford crude product (128 mg, 16.92%), which was used directly without further purification; m/z (LC-MS, ESI+), RT=2.79 (M+H 450.1 & 452.0).

Aufarbeitung

  1. temperatureThe resulting mixture was heated further
  2. temperaturethen cooled
  3. customThe residue was triturated, with sonication, under ethanol (˜25 mL)
  4. filtrationsolid collected by suction filtration

Quellen und Nachweise

ORD-Eintrag
ord-38e45d7b8a4040939d9ac32bbf0713f4
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129380B2

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