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

HRID 2263334Notes

Reaction equation

HRID 2263334 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:10])[NH2:9])=[CH:4][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:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:10]=1

Participants

6

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 42952384-Fluorobenzamidine

Product 1

HCID 463184735-Chloro-3-(4-fluorophenyl)-1,2,4-thiadiazoleYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluorobenzenecarboximidamide (1.38 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 1.5 hours. 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 1.82 g (84.7%) 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=9:1)

Sources & evidence

ORD record
ord-259a2ee0ef1948938a5b927c093120c6
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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