Hydrochloric Acid → N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 21465

Reaktionsgleichung

Reaktionsgleichung von HRID 21465
C1(C)C=CC(S(O[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)(=O)=O)=CC=1.[F:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([OH:25])=[CH:20][C:19]=1[N:26]1[C:30](=[O:31])[C:29]2[CH2:32][CH2:33][CH2:34][CH2:35][C:28]=2[C:27]1=[O:36].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C>[F:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([O:25][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:20][C:19]=1[N:26]1[C:30](=[O:31])[C:29]2[CH2:32][CH2:33][CH2:34][CH2:35][C:28]=2[C:27]1=[O:36]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1586511H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-HCID 317685Cyclopentyl 4-methylbenzene-1-sulfonate

Produkt 1

HCID 15279390N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimideAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Cyclopentyl p-toluenesulfonate (1.90 g, 8.11 mmol) was added to a solution of N-(2-fluoro-4-chloro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (2.0 g, 6.76 mmol) and potassium carbonate (0.60 g, 4.34 mmol) in acetonitrile (50 ml), followed by stirring for 2 hours at 80° C. After completion of the reaction, 1N hydrochloric acid (20 ml) was added to the resulting reaction mixture, and the mixture was extracted with ethyl acetate (20 ml×3 times). The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Ethanol (5 ml) was added to the resulting pale yellow oily substance, and the precipitated N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydrophthalimide as a white solid (0.77 g, 2.12 mmol, 31.4% yield) was isolated by filtration. The spectral data and the like are as described in Example 1.

Aufarbeitung

  1. additionwas added to the resulting reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate (20 ml×3 times)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionEthanol (5 ml) was added to the resulting pale yellow oily substance

Quellen und Nachweise

ORD-Eintrag
ord-c40429fedc8b48e5945f7903f9fa7bdf
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424277

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