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Chlorosuccinimide → methyl N-[2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoyl]carbamate

HRID 1188000
Notes
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Reaction equation

HRID 1188000 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[O:9])=[C:6]([CH3:17])[CH:5]=1.ClN1C(=O)CCC1=O.[Cl:26][C:27]1[CH:28]=[C:29]([C:35]([C:37]([F:40])([F:39])[F:38])=[CH2:36])[CH:30]=[C:31]([Cl:34])[C:32]=1[Cl:33].C(=O)([O-])O.[K+]>COCCOC.O>[CH3:17][C:6]1[CH:5]=[C:4]([C:3]2[CH2:36][C:35]([C:29]3[CH:30]=[C:31]([Cl:34])[C:32]([Cl:33])=[C:27]([Cl:26])[CH:28]=3)([C:37]([F:40])([F:39])[F:38])[O:1][N:2]=2)[CH:16]=[CH:15][C:7]=1[C:8]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86654469methyl N-[4-hydroxyiminomethyl-2-methylbenzoyl]carbamate

Product 1

HCID 86654471methyl N-[2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoyl]carbamate
Yield 23.7%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

In a solution of 45 mg of methyl N-[4-hydroxyiminomethyl-2-methylbenzoyl]carbamate in 10 mL of 1,2-dimethoxyethane, 40 mg of N-chlorosuccinimide was added, and stirred at 60° C. for 45 minutes. Then, the reaction mixture was left and cooled to room temperature, and then 68 mg of 3,4,5-trichloro-1-(1-trifluoromethylethenyl)benzene, 40 mg of potassium hydrogen carbonate and 5 drops of water were added, and continued to stir at room temperature further for 15 hour. After the completion of the reaction, the reaction mixture was poured in 10 mL of water, and extracted with ethyl acetate (15 mL×2). The combined organic phases were dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (gradient of 1:2 to 1:1) to obtain 23 mg of the aimed product as colorless resinous substance.

Workup

  1. waitThen, the reaction mixture was left
  2. temperaturecooled to room temperature
  3. stirringto stir at room temperature further for 15 hour
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (15 mL×2)
  6. dry with materialdried over saturated sodium chloride aqueous solution
  7. distillationanhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-329cc39c3ece4e5bb578e52b5f49d52b
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673951B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes