Trichloromethanethiol → 5-Chloro-3-(piperidin-1-yl)-1,2,4-thiadiazole

HRID 2263351Notes

Reaction equation

HRID 2263351 reaction equation
Br.[N:2]1([C:8](=[NH:10])[NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Cl:11][C:12]([SH:15])(Cl)Cl.[OH-].[Na+]>C(Cl)Cl.O>[Cl:11][C:12]1[S:15][N:9]=[C:8]([N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[N:10]=1

Participants

6

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 2777304Piperidine-1-carboximidamide Hydrobromide

Product 1

HCID 652671425-Chloro-3-(piperidin-1-yl)-1,2,4-thiadiazoleYield 25.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperidine-1-carboximidamide hydrobromide (2.00 g, 9.61 mmol) and perchloromethyl mercaptan (1.04 ml, 9.61 mmol) in methylene chloride (10 ml) was added dropwise a solution of sodium hydroxide (1.54 g, 38.4 mmol) in water (4 ml) under ice-cooling. The mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The reaction mixture was poured to water, and the organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate=4:1) to give 500 mg (25.6%) of the desired product as a solid.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane: ethyl acetate=4:1)

Sources & evidence

ORD record
ord-00fa34c2e0e34170b563d65845da2b74
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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