Triethylamine → 2-{[(2-Chlorophenyl)methyl]sulfanyl}-5-(trifluoromethyl)-1,3,4-thiadiazole

HRID 839951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 839951
[SH:1][C:2]1[S:3][C:4]([C:7]([F:10])([F:9])[F:8])=[N:5][N:6]=1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Cl>C(O)C>[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][S:1][C:2]1[S:3][C:4]([C:7]([F:10])([F:9])[F:8])=[N:5][N:6]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 119062-Chlorobenzyl chlorideHCID 1785062845-(Trifluoromethyl)-1,3,4-thiadiazole-2(3H)-thione

Produkt 1

HCID 203228742-{[(2-Chlorophenyl)methyl]sulfanyl}-5-(trifluoromethyl)-1,3,4-thiadiazoleAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

9.3 g (0.05 mole) of 2-mercapto-5-trifluoromethyl-1,3,4-thiadiazole, 5.1 g (0.05 mole) of triethylamine and 8.1 g (0.05 mole) of o-chlorobenzyl chloride in 80 ml of absolute ethanol were stirred for 2 hours under nitrogen at 50° C and then poured onto ice. The precipitate was filtered off and purified by low temperature crystallization from petroleum ether. 10 g (64% of theory) of 2-(o-chlorobenzylthio)-5-trifluoromethyl-1,3,4-thiadiazole of melting point 36°-37° C were obtained. A solution of 9.8 g (0.048 mole) of m-chloroperbenzoic acid (85% pure) in 85 ml of methylene chloride was added dropwise to 5 g (0.016 mole) of the above compound in 10 ml of methylene chloride. The mixture was stirred for 4.5 hours under reflux and then mixed successively with a solution of 6.4 g of sodium sulfite in a little water, followed by a solution of 2.7 g of sodium carbonate in a little water, and stirred thoroughly for 15 minutes. The organic phase, after concentration and recrystallization from cyclo-hexane/ethyl acetate, gave colorless crystals. 4.8 g (87% of theory) of 2-(o-chlorobenzylsulfonyl)-5-trifluoromethyl-1,3,4-thiadiazole of melting point 103° C were obtained.

Aufarbeitung

  1. additionpoured onto ice
  2. filtrationThe precipitate was filtered off
  3. custompurified by low temperature crystallization from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-99407eea518b40fe981c97c653c25e18
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04097669

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