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 275103Notes

Reaction equation

HRID 275103 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 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.

Workup

  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

Sources & evidence

ORD record
ord-2fc005605949423b9fd7371d8664c88b
Source dataset
uspto-grants-1995_02
Patent number
US05391807

Reaction notes

Loading…