Triethylamine → 2-[(3,4-Dichlorophenyl)sulfanyl]-5-(trifluoromethyl)-1,3,4-thiadiazole

HRID 839948

Reaktionsgleichung

Reaktionsgleichung von HRID 839948
Br[C:2]1[S:3][C:4]([C:7]([F:10])([F:9])[F:8])=[N:5][N:6]=1.[Cl:11][C:12]1[CH:13]=[C:14]([SH:19])[CH:15]=[CH:16][C:17]=1[Cl:18].C(N(CC)CC)C>C(O)C>[Cl:11][C:12]1[CH:13]=[C:14]([S:19][C:2]2[S:3][C:4]([C:7]([F:10])([F:9])[F:8])=[N:5][N:6]=2)[CH:15]=[CH:16][C:17]=1[Cl:18]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 799643,4-DichlorobenzenethiolHCID 128746852-Bromo-5-(trifluoromethyl)-1,3,4-thiadiazole

Produkt 1

HCID 543536242-[(3,4-Dichlorophenyl)sulfanyl]-5-(trifluoromethyl)-1,3,4-thiadiazoleAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

130.5 g (0.66 mole) of 2-bromo-5-trifluoromethyl-1,3,4-thiadiazole were added dropwise to a solution of 98.1 g (0.66 mole) of 3,4dichloro-thiophenol and 57.6 g (0.66 mole) of triethylamine in 500 ml of ethanol. An exothermic effect was observed and a white precipitate separated out. The mixture was stirred for a further 2 hours under reflux, concentrated to half in vacuo and introduced into 1 liter of ice water. The white precipitate was filtered off, dried over phosphorus pentoxide and recrystallized from about 300 ml of petroleum ether. 147 g (76% of theory) of 2-(3',4' -dichlorophenylthio)-5-trifluoromethyl-1,3,4-thiadiazole of melting point 46° C were obtained.

Aufarbeitung

  1. customa white precipitate separated out
  2. temperatureunder reflux
  3. concentrationconcentrated to half in vacuo
  4. additionintroduced into 1 liter of ice water
  5. filtrationThe white precipitate was filtered off
  6. dry with materialdried over phosphorus pentoxide
  7. customrecrystallized from about 300 ml of petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-67fa17f57c2a4dfcb6a0471ef1a7116b
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04097669

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