Ethanethiol → HCID 118113402, compound

HRID 713672Notes

Reaction equation

HRID 713672 reaction equation
[H-].[Na+].[CH2:3]([SH:5])[CH3:4].C1COCC1.Cl[C:12]1[C:13]([C:19]([N:21]([CH3:33])[C:22]2[CH:27]=[CH:26][C:25]([S:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)=[O:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=1>O>[Cl:18][C:16]1[CH:17]=[C:12]([S:5][CH2:3][CH3:4])[C:13]([C:19]([N:21]([CH3:33])[C:22]2[CH:27]=[CH:26][C:25]([S:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)=[O:20])=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 118205927HCID 118205927, compound

Product 1

HCID 118113402HCID 118113402, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.03 g of 60% sodium hydride (oil-based) was added to a mixture of 1.82 mL of ethanethiol and 59 ml of THF under ice cooling, and the mixture was stirred for 1 hour under ice cooling. A mixture of 8.92 g of 3,5-dichloro-N-methyl-N-(4-trifluoromethylsulfanylphenyl)picolinamide and 59 ml of THF was added to the reaction mixture under ice cooling, and the mixture was stirred at room temperature for 7 hours. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 9.02 g of 5-chloro-3-ethylsulfanyl-N-methyl-N-(4-trifluoromethylsulfanylphenyl)picolinamide (hereinafter, referred to as Compound of Present Invention 158).

Workup

  1. additionwas added to the reaction mixture under ice cooling
  2. stirringthe mixture was stirred at room temperature for 7 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ec95089dfb2743a09a35c9a6de24b243
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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