Tetradecyltrimethylammonium → 2,2-Bis(5-chloro-pyrid-2-yl)oxirane

HRID 371180

Reaktionsgleichung

Reaktionsgleichung von HRID 371180
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=2)=[O:9])=[N:6][CH:7]=1.[I-].[CH3:18][S+](C)(C)=O.CCCCCCCCCCCCCC[N+](C)(C)C.[OH-].[Na+]>O.ClC(Cl)(Cl)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)[CH2:18][O:9]2)=[N:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 14251TetradecyltrimethylammoniumHCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)2×HCID 20274519Bis(5-chloropyridin-2-yl)methanone

Produkt 1

HCID 202745202,2-Bis(5-chloro-pyrid-2-yl)oxirane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 62781,1,1-TrichloroethaneLösungsmittel

Versuchsvorschrift

A mixture of bis-(5-chloropyrid-2-yl)ketone (0.8 g), trimethylsulphoxonium iodide (0.84 g), cetrimide (0.08 g) and sodium hydroxide (3 g) in water (16 ml) and 1,1,1-trichloroethane (30 ml) was stirred vigorously and heated at 70° to 75° C. for 2.5 hours. Further trimethylsulphoxonium iodide (0.86 g) was added and the mixture heated at 75° to 80° C. for a further 2 hours. The mixture was cooled, diluted with water (10 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried over magnesium sulfate and evaporated to yield the crude title compound as a brownish paste (0.8 g), which was used directly.

Aufarbeitung

  1. temperatureheated at 70° to 75° C. for 2.5 hours
  2. temperaturethe mixture heated at 75° to 80° C. for a further 2 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with dichloromethane (3×20 ml)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-60f7680d16274171ac481390664b83f4
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04529799

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