HCID 178473698, compound → HCID 23114892, compound

HRID 1641693Notes

Reaction equation

HRID 1641693 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[N:8]=[CH:7][C:6]([SH-:9]C(=S)OCC)=[CH:5][CH:4]=1>C(O)C.[OH-].[Na+]>[F:16][C:2]([F:1])([F:15])[C:3]1[N:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 178473698HCID 178473698, compound

Product 1

HCID 23114892HCID 23114892, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of O-ethyl S-[6-(trifluoromethyl)pyridin-3-yl]dithiocarbonate (2.67 g, 10.0 mmol) in ethanol (30 ml), 1 N aqueous sodium hydroxide (30 ml) was added, and the resulting mixture was stirred for 2 hours at 50° C. The reaction mixture was cooled to room temperature, and washed with methylene chloride. Subsequently, the aqueous layer was acidified with 1 N hydrochloric acid, and was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure, to obtain 6-(trifluoromethyl)pyridin-3-thiol as a crude product.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with methylene chloride
  3. extractionwas extracted with methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d2279a653994ccb84543a7577d21582
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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