Chlorosuccinimide → N-acetyl-N-(5-chloro-2-pyrimidinyl)-2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid amide

HRID 1187969Notes

Reaction equation

HRID 1187969 reaction equation
[C:1]([N:4]([C:17]1[N:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=1)[C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[N:13][OH:14])=[CH:8][C:7]=1[CH3:15])(=[O:3])[CH3:2].ClN1C(=O)CCC1=O.[Cl:32][C:33]1[CH:34]=[C:35]([C:41]([C:43]([F:46])([F:45])[F:44])=[CH2:42])[CH:36]=[C:37]([Cl:40])[C:38]=1[Cl:39].C(=O)([O-])O.[K+]>COCCOC.O>[C:1]([N:4]([C:17]1[N:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=1)[C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:42][C:41]([C:35]3[CH:36]=[C:37]([Cl:40])[C:38]([Cl:39])=[C:33]([Cl:32])[CH:34]=3)([C:43]([F:46])([F:45])[F:44])[O:14][N:13]=2)=[CH:8][C:7]=1[CH3:15])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86654460N-acetyl-N-(5-chloro-2-pyrimidinyl)-4-hydroxyiminomethyl-2-methyl benzoic acid amide

Product 1

HCID 86654459N-acetyl-N-(5-chloro-2-pyrimidinyl)-2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid amideYield 20.8%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
40 °C

Procedure

In a solution of 30 mg of N-acetyl-N-(5-chloro-2-pyrimidinyl)-4-hydroxyiminomethyl-2-methyl benzoic acid amide in 5 mL of 1,2-dimethoxyethane, 16 mg of N-chlorosuccinic acid imide was added and stirred at 40° C. for 30 minutes. Then the reaction mixture was left and cooled to room temperature, and 24 mg of 3,4,5-trichloro-1-(1-trifluoromethylethenyl)benzene, 10 mg of potassium hydrogen carbonate and 1 drop of water were added, and continued to stir at room temperature for 1.5 hour. After the completion of the reaction, the reaction mixture was poured in 10 mL of water, and extracted with ethyl acetate (10 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 1:3 to 1:1) to obtain 11 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 for 1.5 hour
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (10 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-9c973e7c363a49548cf95d1c6e338d61
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

Loading…