Hydrochloric Acid → methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

HRID 275097

Reaktionsgleichung

Reaktionsgleichung von HRID 275097
[CH:1]1(Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([OH:15])=[CH:10][C:9]=1[NH:16][C:17](=[O:20])[O:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C>[F:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][C:9]=1[NH:16][C:17](=[O:20])[O:18][CH3:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 19042327methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate

Produkt 1

HCID 15766845methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamateAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Cyclopentyl bromide (4.07 g, 27.3 mmol) was added to an acetonitrile solution (50 ml) containing methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate (5.00 g, 22,8 mmol) and potassium carbonate (1.80 g, 13.0 mmol), and the mixture was heated under reflux for 4 hours. After reaction, the reaction liquid was cooled to room temperature, 1N hydrochloric acid (50 ml) was added thereto, and this was extracted with ethyl acetate (50 ml×2). The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed by distillation under reduced pressure to obtain methyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate (5.56 g, 19.3 mmol). Yield: 84.8%.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customAfter reaction
  4. customthe reaction liquid
  5. extractionthis was extracted with ethyl acetate (50 ml×2)
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe drying agent was removed by filtration
  9. customthe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3756c97c09dc4e36832c364b3c3517c9
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391807

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