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Dichloromethane → N-Methyl-N-phenyl-2-(3-trifluoromethyl-4-phenyl-5-isoxazolyloxy)acetamide

HRID 477389
Notes
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Reaction equation

HRID 477389 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](=[O:6])[CH2:4][OH:5].CC(C)([O-])C.[K+].[F:19][C:20]([F:34])([F:33])[C:21]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:24](Cl)[O:23][N:22]=1.C(Cl)Cl>C1COCC1>[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](=[O:6])[CH2:4][O:5][C:24]1[O:23][N:22]=[C:21]([C:20]([F:34])([F:33])[F:19])[C:25]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 57434772-hydroxy-N-methyl-N-phenylacetamideHCID 143710873-Trifluoromethyl-4-phenyl-5-chloroisoxazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 14855465N-Methyl-N-phenyl-2-(3-trifluoromethyl-4-phenyl-5-isoxazolyloxy)acetamideYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.99 g (6.0 mmole) of N-methyl-N-phenyl-2-hydroxyacetamide was dissolved in THF (6 ml) and the solution was mixed with 0.75 g (6.0 mmole) of 90% potassium t-butoxide with ice cooling. The mixture was stirred for 30 minutes and then 1.24 g (5.0 mmole) of 3-trifluoromethyl-4-phenyl-5-chloroisoxazole was added dropwise to the mixture. After being stirred for 30 minutes, the mixture was refluxed for 24 hours. After cooling the reaction mixture, 60 ml of methylene chloride was added and the mixture was washed with a 5% solution of HCl and water. The methylene chloride phase was evaporated under reduced pressure and the residue was purified by chromatography on silica gel to give 1.15 g of colorless crystals. These were recrystallized from n-hexane to give 950 mg of the titled compound, yield 50.5%, m.p. 93.0°-94.0° C.

Workup

  1. stirringAfter being stirred for 30 minutes
  2. temperaturethe mixture was refluxed for 24 hours
  3. additionwas added
  4. washthe mixture was washed with a 5% solution of HCl and water
  5. customThe methylene chloride phase was evaporated under reduced pressure
  6. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-12a55684be7d46a5b9a3bebeb88e07a2
Source dataset
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04888044

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes