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

HRID 2263342

Reaktionsgleichung

Reaktionsgleichung von HRID 2263342
Cl.[O:2]([CH2:9][C:10](=[NH:12])[NH2:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:13][C:14]([SH:17])(Cl)Cl.[OH-].[Na+]>ClCCl.O>[Cl:13][C:14]1[S:17][N:11]=[C:10]([CH2:9][O:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:12]=1

Komponenten

6

Edukt 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 27459122-Phenoxyacetamidine Hydrochloride

Produkt 1

HCID 542746325-Chloro-3-(phenoxymethyl)-1,2,4-thiadiazoleAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-phenoxyethanimidamide hydrochloride (2.00 g, 10.7 mmol) and perchloromethyl mercaptan (1.15 ml, 10.7 mmol) in dichloromethane (40 ml) was added dropwise a solution of sodium hydroxide (2.15 g, 53.7 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 a silica gel column chromatography (hexane:ethyl acetate=9:1) to give 1.66 g (68.3%) of the desired product as an oil.

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 a silica gel column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-fcfa0584cefd49f9885b73cf65052a7a
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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