Ethyl chloroformate → 3-(3,4-Dichlorophenyl)-5-methyl-5-(trifluoromethyl)oxazolidine-2,4-dione

HRID 1274440Notes

Reaction equation

HRID 1274440 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])[C:11]([OH:17])([CH3:16])[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].Cl[C:22](OCC)=[O:23]>C1COCC1.[Na].C(C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:10](=[O:18])[C:11]([CH3:16])([C:12]([F:14])([F:15])[F:13])[O:17][C:22]2=[O:23])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 15847286HCID 15847286, compound

Product 1

HCID 221211393-(3,4-Dichlorophenyl)-5-methyl-5-(trifluoromethyl)oxazolidine-2,4-dioneYield 38.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 66591377Sodium benzophenoneSolvent

Procedure

3 g of N-(3,4-dichlorophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide were dissolved in 50 ml of THF distilled beforehand over sodium/benzophenone. 1 g of sodium hydride (NaH), at 60% in oil, was added. The reaction mixture was stirred for 30 min and then cooled to 0-5°. 2.3 g of ethyl chloroformate, in solution in 10 ml of THF, were added without exceeding 5° C. After maintaining overnight at room temperature, the reaction mixture was poured onto 100 ml of ice-cold water and then extracted with 4×50 ml of dichloromethane. The organic phase was washed with 20% sodium chloride, dried over sodium sulfate and evaporated to dryness. The residue was purified by silica chromatography (eluent: 1/1 heptane/dichloromethane). 1.25 g of 3-(3,4-dichlorophenyl)-5-methyl-5-(trifluoromethyl)oxazolidine-2,4-dione was obtained, for a yield 38%.

Workup

  1. temperaturecooled to 0-5°
  2. customwithout exceeding 5° C
  3. extractionextracted with 4×50 ml of dichloromethane
  4. washThe organic phase was washed with 20% sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by silica chromatography (eluent: 1/1 heptane/dichloromethane)

Sources & evidence

ORD record
ord-714fa32092164427bfa59377aed46eee
Source dataset
uspto-grants-2000_12
Patent number
US06156899

Reaction notes

Loading…