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

HRID 2263336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263336
Cl.[F:2][C:3]1[CH:4]=[C:5]([C:9](=[NH:11])[NH2:10])[CH:6]=[CH:7][CH:8]=1.[Cl:12][C:13]([SH:16])(Cl)Cl.[OH-].[Na+]>ClCCl.O>[Cl:12][C:13]1[S:16][N:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=2)[N:11]=1

Komponenten

6

Edukt 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 124561593-Fluorobenzene-1-carboximidamide--hydrogen chloride (1/1)

Produkt 1

HCID 463184475-Chloro-3-(3-fluorophenyl)-1,2,4-thiadiazoleAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-fluorobenzenecarboximidamide hydrochloride (1.75 g, 10.0 mmol) and perchloromethyl mercaptan (1.07 ml, 10.0 mmol) in dichloromethane (20 ml) was added dropwise a solution of sodium hydroxide (2.00 g, 50.0 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 1.52 g (71.0%) of the desired product as a solid.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f801b3ae1e6147238cf850d4acef24cc
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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