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

HRID 21487

Reaktionsgleichung

Reaktionsgleichung von HRID 21487
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)(=O)=O)=CC=1.Cl>CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:4][C:3]=1[NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 317685Cyclopentyl 4-methylbenzene-1-sulfonateHCID 19374488benzyl N-(4-chloro-2-fluoro-5-hydroxyphenyl)carbamate

Produkt 1

HCID 19374482benzyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Then, benzyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate (12.2 g, 41.3 mmol), potassium carbonate (5.97 g, 432.1 mmol), cyclopentyl p-toluenesulfonate (11.2 g, 46.4 mmol) and acetone (150 ml) as a solvent were charged into a 500 cc round-bottom Flask and heated for 9 hours while refluxing. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid. After thoroughly stirring, the precipitated benzyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate as a pale yellow solid (14.9 g, 40.9 mmol, 994 yield) was isolated by filtration and well dried. 1H-NMR Spectrum (CDCl3, TMS, ppm): δ1.48-2.07 (8H, m), 4.83 (1H, m), 5.26 (2H, s), 6 92 (1H, br, s) 7.14 (1H, d, JHF =11.5 Hz), 7.47 (5H, s), 7.93 (1H, d, JHF =8.3 Hz).

Aufarbeitung

  1. temperatureheated for 9 hours
  2. temperaturewhile refluxing
  3. customAfter completion of the reaction

Quellen und Nachweise

ORD-Eintrag
ord-84136efc65e547e584fd1568e04a12b0
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424277

Verknüpfte Notizen

Wird geladen…