Triethylamine → HCID 59355632, compound

HRID 1627009Notes

Reaction equation

HRID 1627009 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[N:10][OH:11])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:2].ClN1C(=O)CCC1=O.[Cl:23][C:24]1[CH:25]=[C:26]([C:31]([C:33]([F:36])([F:35])[F:34])=[CH2:32])[CH:27]=[C:28]([Cl:30])[CH:29]=1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:23][C:24]1[CH:25]=[C:26]([C:31]2([C:33]([F:36])([F:34])[F:35])[O:11][N:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=3)[CH2:32]2)[CH:27]=[C:28]([Cl:30])[CH:29]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 53628322HCID 53628322, compound

Product 1

HCID 59355632HCID 59355632, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In dimethylformamide (40 mL), 2-ethyl-5-hydroxyiminomethylnitrobenzene (4.30 g) and N-chlorosuccinimide (2.97 g) were dissolved, and the mixture was stirred at 60° C. for 1 hour. The reaction mixture was cooled to room temperature, and thereto was added 2-(3,5-dichlorophenyl)-3,3,3-trifluoro-1-propene (3.5 g), followed by triethylamine (1.7 g), and then the mixture was stirred for 6 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-ethylnitrobenzene (5.74 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred for 6 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-959591e2791140ecbf19607c26a0c240
Source dataset
uspto-grants-2014_07
Patent number
US08785485B2

Reaction notes

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