Trichloromethanethiol → HCID 46318466, compound

HRID 2263348Notes

Reaction equation

HRID 2263348 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[NH:10])[NH2:9])[CH:3]=1.[Cl:11][C:12]([SH:15])(Cl)Cl.[OH-].[Na+]>ClCCl.O>[Cl:11][C:12]1[S:15][N:9]=[C:8]([C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)[N:10]=1

Participants

6

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 202042Nicotinamidine hydrochloride

Product 1

HCID 46318466HCID 46318466, compoundYield 4.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of pyridine-3-carboximidamide hydrochloride (2.00 g, 12.7 mmol) and perchloromethyl mercaptan (1.75 ml, 16.3 mmol) in dichloromethane (40 ml) was added dropwise a solution of sodium hydroxide (3.26 g, 81.5 mmol) in water (6 ml) under ice-cooling. Then, the reaction mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The organic layer was separated, washed with water, and then 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=1:1) to give 110 mg (4.38%) of the desired product as a solid.

Workup

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

Sources & evidence

ORD record
ord-fd7f9eb52a4140d984b87d9ac77725d5
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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