Sulfuric Acid → HCID 178520209, Verbindung

HRID 1106786

Reaktionsgleichung

Reaktionsgleichung von HRID 1106786
[Cl:1][C:2]1([C:5]([OH:20])([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:4][CH2:3]1.C([Li])CCC.[S].[S:27](=O)(=O)(O)O>CCCCCC.O1CCCC1>[Cl:1][C:2]1([C:5]([OH:20])([CH2:14][N:15]2[C:19]([SH:27])=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:3][CH2:4]1

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 119361alpha-(1-Chlorocyclopropyl)-alpha-((2-chlorophenyl)methyl)-1H-1,2,4-triazole-1-ethanolHCID 5362487SulfurHCID 178418339Butyllithium

Produkt 1

HCID 178520209HCID 178520209, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

At -20° C., a mixture of 3.12 g (10 mmol) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol and 45 ml of absolute tetrahydrofuran is admixed with 8.4 ml (21 mmol) of n-butyllithium in hexane and stirred at 0° C. for 30 minutes. The reaction mixture is then cooled to -70° C., admixed with 0.32 g (10 mmol) of sulphur powder and stirred at -70° C. for 30 minutes. The mixture is warmed to -10° C., admixed with ice-water and adjusted to pH 5 by addition of dilute sulphuric acid. The mixture is extracted repeatedly with ethyl acetate and the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. In this manner, 3.2 g (93% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol are obtained in the form of a solid substance which, after recrystallization, melts at 138-139° C.

Aufarbeitung

  1. temperatureThe reaction mixture is then cooled to -70° C.
  2. stirringstirred at -70° C. for 30 minutes
  3. temperatureThe mixture is warmed to -10° C.
  4. extractionThe mixture is extracted repeatedly with ethyl acetate
  5. dry with materialthe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2caf5cbefd3844d9b722fa231dbb8fc8
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057353

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