Water → HCID 86642369, compound

HRID 1642753Notes

Reaction equation

HRID 1642753 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[S-:28][C:29]#[N:30].[K+].O.[NH3:33].O>O1CCCC1>[C:29]([NH:33][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:23])(=[S:28])[NH2:30]

Participants

6

Reactant 4

HCID 962WaterHCID 516872Potassium thiocyanateHCID 12896473Azane;hydrateHCID 866114794-(5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride

Product 1

HCID 86642369HCID 86642369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g of 4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride synthesized in Process 4 of Synthetic Example 1 in 20 mL of tetrahydrofuran, 245 mg of potassium thiocyanate was added and the resultant mixture was stirred at 40° C. for 1 hour. Next, the reaction mixture was left to be cooled to room temperature and 5 mL of concentrated ammonia water was added to the reaction mixture, followed by continuing the stirring of the mixture for another 30 minutes. After the completion of the reaction, 20 mL of water was added to the reaction mixture to dilute the mixture and the diluted reaction mixture was extracted with 40 mL of ethyl acetate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.9 g of the objective substance as a colorless resin-state substance.

Workup

  1. waitNext, the reaction mixture was left
  2. additionwas added to the reaction mixture
  3. additionto dilute the mixture
  4. customthe diluted reaction mixture
  5. extractionwas extracted with 40 mL of ethyl acetate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography
  8. washeluting with ethyl acetate-hexane (1:1)
  9. customto obtain 0.9 g of the objective substance as a colorless resin-state substance

Sources & evidence

ORD record
ord-5fca73846a6b468f82922cabd4b05114
Source dataset
uspto-grants-2012_02
Patent number
US08119671B2

Reaction notes

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