Ethanol → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

HRID 275099

Reaktionsgleichung

Reaktionsgleichung von HRID 275099
[OH-].[K+].C(O)C.[F:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][C:8]=1[NH:20]C(=O)OC>O>[F:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][C:8]=1[NH2:20]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 15766845methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

Produkt 1

HCID 152793894-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamineAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4N potassium hydroxide aqueous solution (4.75 liters) was added to an ethanol solution (3 liters) of methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate (2.25 kg, 7.85 mol) and the mixture was heated under reflux for 5 hours. After reaction, the reaction liquid was cooled to room temperature, water (5 liters) was added thereto, and this was extracted with toluene (5 liters×2). The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The drying agent was taken out by filtration, and the solvent was removed by distillation under reduced pressure to obtain an oily product of 2-fluoro-4-chloro-5-cyclopentyloxyaniline (1.75 kg, 7.62 mol). Yield: 98.3%. Spectral data and other data of the product are those as shown in Example 21.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customAfter reaction
  4. customthe reaction liquid
  5. extractionthis was extracted with toluene (5 liters×2)
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was taken out by filtration
  9. customthe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-26a7ca6f0d9d415bb97985d3cdfe3487
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391807

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