Water → N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 21478

Reaktionsgleichung

Reaktionsgleichung von HRID 21478
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:3]=1[NH2:4].[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2[CH2:21][CH2:22][CH2:23][CH2:24][C:16]1=2.O>C(O)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:3]=1[N:4]1[C:18](=[O:19])[C:17]2[CH2:21][CH2:22][CH2:23][CH2:24][C:16]=2[C:15]1=[O:20]

Komponenten

5

Edukt 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 107989305-Amino-2-chloro-4-fluorophenyl methyl carbonate

Produkt 1

HCID 19374481N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimideAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 2-fluoro-4-chloro-5-methoxycarbonyloxyaniline (20.0 g, 91.1 mmol) and 3,4,5,6-tetrahydrophthalic anhydride (14.0 g, 92.0 mmol) in acetic acid (200 ml) was reacted for 5 hours while heating under refluxing. After completion of the reaction, the mixture was-cooled to room temperature, water (200 ml) was added thereto, and extracted with ethyl acetate (100 ml×3 times). The organic layer was washed with an aqueous solution of sodium carbonate and water, dried, and the solvent was distilled off under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent: ethyl acetate/hexane=1/5) to obtain N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimide as a white solid (26.2 g, 72.1 mmol, 79.2% yield).

Aufarbeitung

  1. temperaturewhile heating
  2. temperatureunder refluxing
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (100 ml×3 times)
  5. washThe organic layer was washed with an aqueous solution of sodium carbonate and water
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting oily substance was purified by silica gel column chromatography (development solvent: ethyl acetate/hexane=1/5)

Quellen und Nachweise

ORD-Eintrag
ord-09cb1a08229048beaa4bbad76741f767
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424277

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