Potassium Bicarbonate → HCID 25144318, compound

HRID 1844822Notes

Reaction equation

HRID 1844822 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:9])=[C:6]([CH3:20])[CH:5]=1.[Cl:21][C:22]1[CH:23]=[C:24]([C:29]([C:31]([F:34])([F:33])[F:32])=[CH2:30])[CH:25]=[C:26]([Cl:28])[CH:27]=1.C(=O)([O-])O.[K+]>CN(C)C=O>[Cl:21][C:22]1[CH:23]=[C:24]([C:29]2([C:31]([F:34])([F:32])[F:33])[O:1][N:2]=[C:3]([C:4]3[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=4)=[O:9])=[C:6]([CH3:20])[CH:5]=3)[CH2:30]2)[CH:25]=[C:26]([Cl:28])[CH:27]=1

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86070635HCID 86070635, compound

Product 1

HCID 25144318HCID 25144318, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In a solution of 0.45 g of 4-hydroxyiminomethyl-2-methyl-N-(2-pyridylmethyl) benzoic acid amide in 10 ml of N,N-dimethylformamide, 0.25 g of N-chlorosuccinc acid imide was added, and stirred at 70° C. for 1 hour. Then, the reaction mixture was left and cooled to room temperature, 0.41 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.25 g of potassium hydrogen carbonate were added, and stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (60 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1), and 0.30 g of the aimed product was obtained as white crystal.

Workup

  1. waitThen, the reaction mixture was left
  2. temperaturecooled to room temperature
  3. stirringstirred at room temperature for 3 hours
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (60 ml×1)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-e81fb815586f4780ba0b9fe575b29faa
Source dataset
uspto-grants-2015_02
Patent number
US08946492B2

Reaction notes

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