Potassium Carbonate → 3-{5-[(But-3-yn-2-yl)oxy]-4-chloro-2-fluorophenyl}-5-(propan-2-ylidene)-1,3-oxazolidine-2,4-dione

HRID 1198786Notes

Reaction equation

HRID 1198786 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 1831483-{5-[(But-3-yn-2-yl)oxy]-4-chloro-2-fluorophenyl}-5-(propan-2-ylidene)-1,3-oxazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Acetonitrile (50 ml) was added to a mixture comprising N-(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 1 N 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.

Workup

  1. temperaturethe reaction mixture was heated for 4 hours
  2. temperatureunder reflux
  3. customwas removed by distillation under reduced pressure, and 1 N 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

Sources & evidence

ORD record
ord-b04cc22bf31f4d47a9c2fba47a56a67d
Source dataset
uspto-grants-1994_01
Patent number
US05281742

Reaction notes

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