Dichloromethane → 5-Chloro-3-(4-chlorophenyl)-1,2,4-thiadiazole

HRID 2263339Notes

Reaction equation

HRID 2263339 reaction equation
I.F[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[NH:11])[NH2:10])=[CH:5][CH:4]=1.[Cl:12][C:13]([SH:16])(Cl)Cl.[OH-].[Na+].[Cl:19]CCl>O>[Cl:19][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:11]=[C:13]([Cl:12])[S:16][N:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 687807754-Fluorobenzenecarboximidamide hydroiodide

Product 1

HCID 463184645-Chloro-3-(4-chlorophenyl)-1,2,4-thiadiazoleYield 31.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-fluorobenzenecarboximidamide hydroiodide (5.00 g, 17.7 mmol) and perchloromethyl mercaptan (1.90 ml, 17.7 mmol) in dichloromethane (100 ml) was added dropwise a solution of sodium hydroxide (3.55 g, 88.8 mmol) in water (7 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 1.78 g (31.2%) 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-fa35f56fab774bdeb6cd1281a59fee6f
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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