Methyl chloroformate → Methyl N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methylbenzoyl]-N-(2,2,2-trifluoroethoxymethyl)carbamate

HRID 878823Notes

Reaction equation

HRID 878823 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:31]([F:34])([F:33])[F:32])[O:13][N:12]=[C:11]([C:14]3[CH:29]=[CH:28][C:17]([C:18]([NH:20][CH2:21][O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[O:19])=[C:16]([CH3:30])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].Cl[C:38]([O:40][CH3:41])=[O:39]>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:31]([F:32])([F:34])[F:33])[O:13][N:12]=[C:11]([C:14]3[CH:29]=[CH:28][C:17]([C:18]([N:20]([CH2:21][O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:38](=[O:39])[O:40][CH3:41])=[O:19])=[C:16]([CH3:30])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 252170234-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethoxymethyl)benzoic acid amide

Product 1

HCID 25218095Methyl N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methylbenzoyl]-N-(2,2,2-trifluoroethoxymethyl)carbamateYield 12.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a solution of 0.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethoxymethyl)benzoic acid amide in 10 mL of N,N-dimethylformamide, 0.0825 g of 60% oily sodium hydride was added under cooling with ice and with stirring, and stirred at room temperature for 10 minutes. Then, 0.268 g of methyl chloroformate was added, and continued to stir at the same temperature for 30 minutes. After the completion of the reaction, the reaction was poured in 50 mL of water, extracted with ethyl acetate (50 mL×1), the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 0.07 g of the aimed product as colorless resinous substance.

Workup

  1. temperatureunder cooling with ice
  2. stirringstirred at room temperature for 10 minutes
  3. stirringto stir at the same temperature for 30 minutes
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (50 mL×1)
  6. dry with materialdried over saturated sodium chloride aqueous solution
  7. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-921ae639a48845f9a9603818a5a615be
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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