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Dimethylformamide → 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amide

HRID 878803
Notes
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Reaction equation

HRID 878803 reaction equation
CN(C)C=O.[NH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[N:8]1.[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2([C:35]([F:38])([F:37])[F:36])[O:24][N:23]=[C:22]([C:25]3[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[C:27]([CH3:34])[CH:26]=3)[CH2:21]2)[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(OCC)(=O)C>CN(C)C(=O)C>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2([C:35]([F:37])([F:36])[F:38])[O:24][N:23]=[C:22]([C:25]3[CH:33]=[CH:32][C:28]([C:29]([NH:6][N:7]4[CH:11]=[CH:10][CH:9]=[N:8]4)=[O:30])=[C:27]([CH3:34])[CH:26]=3)[CH2:21]2)[CH:16]=[C:17]([Cl:19])[CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 118293521H-pyrazol-1-amineHCID 866114794-(5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride

Product 1

HCID 671639784-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In 4 mL of N,N-dimethylacetamide, 0.23 g of 50% N,N-dimethylformamide solution of 1-aminopyrazole was added, and 0.30 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl-chloride synthesized in Step 4 of Synthetic Example 1 was added at room temperature with stirring, and stirred at the same temperature for 2 hours. After the completion of the reaction, 20 mL of ethyl acetate was added in the reaction mixture, washed with water (20 mL×1), and then the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with neutral alumina column chromatography that was eluated with chloroform to obtain 0.22 g of the aimed product as yellow resinous substance.

Workup

  1. stirringstirred at the same temperature for 2 hours
  2. additionwas added in the reaction mixture
  3. washwashed with water (20 mL×1)
  4. dry with materialdried over saturated sodium chloride aqueous solution
  5. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  6. customThe residue was purified with neutral alumina column chromatography that

Sources & evidence

ORD record
ord-206a3f68af6b4d5f8d59a909ed9864bb
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987464B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes