Methyl iodide → HCID 66756501, compound

HRID 1642754Notes

Reaction equation

HRID 1642754 reaction equation
[C:1]([NH:4][C:5](=[O:30])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:16][C:15]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[O:14][N:13]=2)=[CH:8][C:7]=1[CH3:29])(=[S:3])[NH2:2].[C:31](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.O>[NH2:2][C:1]([S:3][CH3:31])=[N:4][C:5](=[O:30])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:16][C:15]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:18])[F:19])[O:14][N:13]=2)=[CH:8][C:7]=1[CH3:29]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86642369HCID 86642369, compound

Product 1

HCID 66756501HCID 66756501, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.30 g of N-thiocarbamoyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide and 0.26 g of potassium carbonate in 10 mL of N,N-dimethylformamide, 0.107 g of methyl iodide was added and the resultant mixture was stirred at room temperature for 15 hours. After the completion of the reaction, the reaction mixture was diluted with 20 mL of water and the diluted reaction mixture was extracted with ethyl acetate (30 mL×1). The organic phase was dehydrated and dried with saturated brine and over anhydrous sodium sulfate, respectively, in this order, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:3) to obtain 0.28 g of the objective substance as a colorless resin-state substance.

Workup

  1. customAfter the completion of the reaction
  2. customthe diluted reaction mixture
  3. extractionwas extracted with ethyl acetate (30 mL×1)
  4. dry with materialdried with saturated brine and over anhydrous sodium sulfate
  5. distillationrespectively, in this order, and the solvent was distilled off under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate-hexane (1:3)
  8. customto obtain 0.28 g of the objective substance as a colorless resin-state substance

Sources & evidence

ORD record
ord-7ad0c12837bd423cab05e2b77c63f979
Source dataset
uspto-grants-2012_02
Patent number
US08119671B2

Reaction notes

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