Hydrochloric Acid → N-[2-(3,5-dichloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamide

HRID 56043Notes

Reaction equation

HRID 56043 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[C:9]([CH2:15][N+:16]([O-:18])=[O:17])=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1.Cl[CH2:20][NH:21][C:22](=[O:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30].Cl>CN(C)C=O>[Cl:7][C:8]1[C:9]([CH:15]([N+:16]([O-:18])=[O:17])[CH2:20][NH:21][C:22](=[O:33])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]([F:30])([F:32])[F:31])=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 1180714853,5-Dichloro-2-(nitromethyl)pyridineHCID 118071537N-chloromethyl-2-(trifluoromethyl)benzamide

Product 1

HCID 118071633N-[2-(3,5-dichloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamideYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 6.57 g of potassium tert-butoxide in 100 ml of N,N-dimethylformamide, 10.10 g of 3,5-dichloro-2-(nitromethyl)pyridine was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at the same temperature for another 30 minutes. Then, to the reaction mixture, 11.59 g of N-chloromethyl-2-(trifluoromethyl)benzamide in 50 ml of N,N-dimethylformamide was added dropwise with stirring under cooing with ice, and after the addition, the mixture was stirred at room temperature for another 2 hours. After completion of the reaction, the reaction mixture was carefully poured into 100 ml of ice-water, acidified with 10% aqueous hydrochloric acid and extracted with ethyl acetate (100 ml×2). The resulting organic layers were combined, washed with water (100 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 14.00 g of the desired product as a pale yellow resinous substance.

Workup

  1. temperatureunder cooling with ice
  2. additionafter the addition
  3. stirringthe mixture was stirred at the same temperature for another 30 minutes
  4. stirringwith stirring
  5. additionafter the addition
  6. stirringthe mixture was stirred at room temperature for another 2 hours
  7. customAfter completion of the reaction
  8. extractionextracted with ethyl acetate (100 ml×2)
  9. washwashed with water (100 ml×1)
  10. dry with materialdried over saturated aqueous sodium chloride
  11. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-745cd1027d5f499f9af5dfd25d6fbfd3
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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