Potassium Carbonate → 2,4-Oxazolidinedione, 3-(4-chloro-2-fluoro-5-((1-methyl-2-propyn-1-yl)oxy)phenyl)-5-(1-methylethylidene)-

HRID 2225948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2225948
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[C:13](=[C:16]([CH3:18])[CH3:17])[O:12][C:11]1=[O:19].[C:20]1(C)[CH:25]=CC(S(OC(C)C#C)(=O)=O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:21]([CH3:22])[C:20]#[CH:25])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[C:13](=[C:16]([CH3:17])[CH3:18])[O:12][C:11]1=[O:19]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 561098p-Toluenesulfonic acid 1-butyn-3-yl esterHCID 14695585HCID 14695585, Verbindung

Produkt 1

HCID 1831482,4-Oxazolidinedione, 3-(4-chloro-2-fluoro-5-((1-methyl-2-propyn-1-yl)oxy)phenyl)-5-(1-methylethylidene)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Acetonitrile (50 ml) was added to a mixture comprising 3N-(2-fluoro-4-chloro-5-hydroxyphenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione (5.0 g, 15.7 mmol), 1-butyn-3-yl p-toluenesulfonate (4.0 g, 17.8 mmol) and potassium carbonate (1.5 g, 10.9 mmol), and the reaction mixture was heated for 4 hours under reflux. After reaction, acetonitrile was removed by distillation under reduced pressure, and 1N hydrochloric acid (100 ml) was added to the residue, which was then extracted with ether (50 ml×2). After dried, ether was removed by distillation under reduced pressure, and an oily product of 3N-{2-fluoro-4-chloro-5-(1-butyn-3-yl)oxyphenyl}-5-isopropylidene-1,3-oxazolidine-2,4-dione was obtained. This was recrystallized from ether/hexane, and a pure product (4.94 g, 14.6 mmol) was obtained. Yield: 83.6%. Spectral and other data of the product are those as shown in Example 30.

Aufarbeitung

  1. temperaturethe reaction mixture was heated for 4 hours
  2. temperatureunder reflux
  3. customwas removed by distillation under reduced pressure, and 1N hydrochloric acid (100 ml)
  4. additionwas added to the residue, which
  5. extractionwas then extracted with ether (50 ml×2)
  6. customAfter dried
  7. customether was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f63ffdca16a441cbb7e6a1126e299925
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05344953

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