Triethylamine → HCID 67190472, compound

HRID 386731Notes

Reaction equation

HRID 386731 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:14]=[CH:13][C:7]([CH2:8][NH:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.ClN1C(=O)CCC1=O.[Cl:23][C:24]1[CH:29]=[C:28]([C:30]([C:32]([F:35])([F:34])[F:33])=[CH2:31])[CH:27]=[C:26]([Cl:36])[CH:25]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[Cl:23][C:24]1[CH:29]=[C:28]([C:30]2([C:32]([F:35])([F:33])[F:34])[O:1][N:2]=[C:3]([C:4]3[CH:14]=[CH:13][C:7]([CH2:8][NH:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=3)[CH2:31]2)[CH:27]=[C:26]([Cl:36])[CH:25]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 72275883HCID 72275883, compound

Product 1

HCID 67190472HCID 67190472, compoundYield 26.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-{4-[(hydroxyimino)methyl]benzyl}acetamide (0.5 g) was dissolved in N,N-dimethylformamide (20 mL), N-chlorosuccinimide (0.38 g) was added to this solution, and the mixture was stirred for two hours at room temperature. To the reaction solution, 1,3-dichloro-5-[1-(trifluoromethyl)vinyl]benzene (0.75 g) was added, and after the mixture was cooled to 0° C., a solution of triethylamine (0.58 g) in N,N-dimethylformamide (2 mL) was added dropwise to the mixture, which was then stirred for 8 hours at room temperature. After addition of water and extraction with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then purified by silica gel chromatography to yield N-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]benzyl}acetamide (0.3 g).

Workup

  1. temperatureafter the mixture was cooled to 0° C.
  2. stirringwas then stirred for 8 hours at room temperature
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-9d953f187fa844e79402687537b0df7c
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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