Chloroform → N-(2-chloro-6-trifluoromethylpyridin-3-yl)-2,2-dimethylpropionamide

HRID 923808Notes

Reaction equation

HRID 923808 reaction equation
[NH2:1][C:2]1[C:3]([Cl:12])=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.C(Cl)(Cl)Cl.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>O>[Cl:12][C:3]1[C:2]([NH:1][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:7][CH:6]=[C:5]([C:8]([F:9])([F:11])[F:10])[N:4]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 27376462-Chloro-6-(trifluoromethyl)pyridin-3-amine

Product 1

HCID 86708229N-(2-chloro-6-trifluoromethylpyridin-3-yl)-2,2-dimethylpropionamideYield 117.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-amino-2-chloro-6-trifluoromethylpyridine (3.93 g) and chloroform (30 ml), pivaloyl chloride (2.65 g) and triethylamine (4.04 g) were added under ice-cooling, and stirred at room temperature for 2 hours, then at 60° C. for 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 6.59 g of N-(2-chloro-6-trifluoromethylpyridin-3-yl)-2,2-dimethylpropionamide.

Workup

  1. additionwere added under ice-
  2. temperaturecooling
  3. waitat 60° C. for 2 hours
  4. temperatureInto the reaction mixture cooled to room temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-295281ee170c4124ab0a29e1593b6fdf
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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