Dimethylformamide → HCID 118113415, compound

HRID 713646Notes

Reaction equation

HRID 713646 reaction equation
[CH2:1]([S-:3])[CH3:2].[Na+].Cl[C:6]1[C:7]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1.CN(C=O)C>O>[CH2:1]([S:3][C:6]1[C:7]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][CH:16]=2)=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4459711Sodium ethanethiolateHCID 118113315HCID 118113315, compound

Product 1

HCID 118113415HCID 118113415, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

0.91 g of sodium ethanethiolate was added to a mixture of 1.29 g of 3-chloro-N-(4-trifluoromethylphenyl)picolinamide and 3 mL of DMF, and the mixture was stirred at 60° C. for 2 hours. The reaction mixture cooled to room temperature was poured to water, and the precipitated solid was taken by filtration. The resulting solid was dissolved in ethyl acetate, and the mixture was extracted with water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1.37 g of 3-ethylsulfanyl-N-(4-trifluoromethylphenyl)picolinamide (hereinafter, referred to as Compound of Present Invention 9).

Workup

  1. temperatureThe reaction mixture cooled to room temperature
  2. filtrationthe precipitated solid was taken by filtration
  3. dissolutionThe resulting solid was dissolved in ethyl acetate
  4. extractionthe mixture was extracted with water and ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea9d9db208224006a10fc30fa7f0deee
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

Loading…