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Methyl chloroformate → Methyl n-(5-cyano-2-pyridyl)-n-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]carbamate

HRID 552625
Notes
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Reaction equation

HRID 552625 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:37])[C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:23][C:22]([C:28]4[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=4)([C:24]([F:27])([F:26])[F:25])[O:21][N:20]=3)=[CH:15][C:14]=2[CH3:36])=[N:9][CH:10]=1)#[N:4].[H][H].Cl[C:41]([O:43][CH3:44])=[O:42]>O1CCCC1>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]([C:12](=[O:37])[C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:23][C:22]([C:28]4[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=4)([C:24]([F:27])([F:26])[F:25])[O:21][N:20]=3)=[CH:15][C:14]=2[CH3:36])[C:41](=[O:42])[O:43][CH3:44])=[N:9][CH:10]=1)#[N:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 67164147N-(5-cyano-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl benzoic acid amideHCID 178418361HCID 178418361, compound

Product 1

HCID 67165458Methyl n-(5-cyano-2-pyridyl)-n-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]carbamate
Yield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a suspension of 0.03 g of 55% oily sodium hydride suspended in 3 mL of tetrahydrofuran, a solution of 0.26 g of N-(5-cyano-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl benzoic acid amide in 3 mL of tetrahydrofuran was added under cooling with ice and with stirring and continued to stir at the same temperature for 10 minutes. After ceasing the generation of hydrogen gas, 0.07 g of methyl chloroformate was added, ice bath was removed and continued to stir further for 7 hours. After the completion of the reaction, the reaction mixture was poured in 10 mL of ice water, extracted with ethyl acetate (10 mL×2), the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium 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 (1:2) to obtain 0.24 g of the aimed product as colorless resinous substance.

Workup

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

Sources & evidence

ORD record
ord-34d4e1f1678b4a22b0b7bb34a0e0dcd6
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07951828B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes