Methyl chloroformate → HCID 86654451, compound

HRID 878806Notes

Reaction equation

HRID 878806 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:34])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=4)([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=3)=[CH:12][C:11]=2[CH3:33])=[N:6][CH:7]=1.[H-].[Na+].[H][H].Cl[C:40]([O:42][CH3:43])=[O:41]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:9](=[O:34])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=4)([C:21]([F:23])([F:24])[F:22])[O:18][N:17]=3)=[CH:12][C:11]=2[CH3:33])[C:40](=[O:41])[O:42][CH3:43])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 86654450HCID 86654450, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86654451HCID 86654451, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 0.30 g of N-(5-chloro-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid amide in 3 mL of tetrahydrofuran, 0.037 g of 60% oily sodium hydride was added and stirred at room temperature for 10 minutes. After ceasing the generation of hydrogen gas, 0.080 g of methyl chloroformate was added under cooling with ice and with stirring, and continued to stir at the same temperature further for 10 minutes. After the completion of the reaction, the reaction mixture was poured in 10 mL of ice water, extracted with ethyl acetate (10 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 (2:3) to obtain 0.29 g of the aimed product as yellow resinous substance.

Workup

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

Sources & evidence

ORD record
ord-b49ef6cb273e4b658fb571ff1b109030
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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