Trichloromethanethiol → 5-Chloro-3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazole

HRID 2263341Notes

Reaction equation

HRID 2263341 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[NH:12])[NH2:11])=[CH:6][CH:5]=1.[Cl:15][C:16]([SH:19])(Cl)Cl.[OH-].[Na+]>ClCCl.O>[Cl:15][C:16]1[S:19][N:11]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([F:13])([F:14])[F:2])=[CH:9][CH:8]=2)[N:12]=1

Participants

6

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 125357914-(Trifluoromethyl)benzamidine Hydrochloride

Product 1

HCID 186966075-Chloro-3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazoleYield 29.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(trifluoromethyl)benzenecarboximidamide hydrochloride (2.60 g, 10.0 mmol) and perchloromethyl mercaptan (1.07 ml, 10.0 mmol) in dichloromethane (10 ml) was added dropwise a solution of sodium hydroxide (1.60 g, 40.0 mmol) in water (4 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=9:1) to give 770 mg (29.2%) of the desired product as an oil.

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=9:1)

Sources & evidence

ORD record
ord-12dcd02f7a86498fa787f8ca15f656bd
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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