Dimethylformamide → HCID 118113384, compound

HRID 713636Notes

Reaction equation

HRID 713636 reaction equation
[H-].[Na+].[CH2:3]([SH:5])[CH3:4].CN(C=O)C.Cl[C:12]1[C:13]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)=[O:23])=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1>O>[CH2:3]([S:5][C:12]1[C:13]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][N:26]=2)=[O:23])=[N:14][CH:15]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:17]=1)[CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 118113275HCID 118113275, compound

Product 1

HCID 118113384HCID 118113384, compoundYield 107.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.37 g of 60% sodium hydride (oil-based) was added to a mixture of 0.34 g of ethyl mercaptan and 3 mL of DMF under ice cooling, and the mixture was stirred at room temperature for 10 minutes. 1.35 g of 3-chloro-5-trifluoromethyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide was added to the reaction mixture, and the mixture was stirred at room temperature for 3 hours. Water was poured to the reaction mixture, and the precipitated solid was taken by filtration and dried under reduced pressure to obtain 1.55 g of 3-ethylsulfanyl-5-trifluoromethyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide (hereinafter, referred to as Compound of Present Invention 1).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. filtrationthe precipitated solid was taken by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-e634025adb3e4a51ab1221d3f4909269
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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