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Triethylamine → 4-[5-(3,5-Dichloro-4-cyano-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester

HRID 1027600
Notes
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Reaction equation

HRID 1027600 reaction equation
[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[N:14][OH:15])=[CH:9][C:8]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2].ClN1C(=O)CCC1=O.[Cl:26][C:27]1[CH:34]=[C:33]([C:35]([C:37]([F:40])([F:39])[F:38])=[CH2:36])[CH:32]=[C:31]([Cl:41])[C:28]=1[C:29]#[N:30].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:36][C:35]([C:33]3[CH:32]=[C:31]([Cl:41])[C:28]([C:29]#[N:30])=[C:27]([Cl:26])[CH:34]=3)([C:37]([F:38])([F:40])[F:39])[O:15][N:14]=2)=[CH:9][C:8]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31398Chlorosuccinimide2×HCID 672474602,6-Dichloro-4-(1-trifluoromethyl-vinyl)-benzonitrileHCID 723270964-(Hydroxyimino-methyl)-2-methyl-benzoic acid tert-butyl ester

Product 1

HCID 672466894-[5-(3,5-Dichloro-4-cyano-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester
Yield 35.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(hydroxyimino-methyl)-2-methyl-benzoic acid tert-butyl ester (1.47 g) in N, N-dimethylformamide (13 ml) was added N-chlorosuccinimide (“NCS”) (832 mg). The reaction mixture was stirred at ambient temperature for 2 hours. More N-chlorosuccinimide (“NCS”) (850 mg) was added and the reaction mixture was stirred at ambient temperature for 1 hour. A solution of 2,6-Dichloro-4-(1-trifluoromethyl-vinyl)-benzonitrile (1.37 g) and triethylamine (0.72 ml) in N,N-dimethylformamide (13 ml) was added dropwise to the reaction mixture. The reaction mixture was stirred at ambient temperature for 17 hours. Water and ethyl acetate were added and the phases were separated. The organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel to give 4-[5-(3,5-Dichloro-4-cyano-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester (0.902 g). 19F-NMR (CDCl3, 75 MHz): −78.93 ppm.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 1 hour
  2. stirringThe reaction mixture was stirred at ambient temperature for 17 hours
  3. customthe phases were separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-48790eaf2d4b42db9048f5a9538ef24d
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735362B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes