Phosgene → HCID 23042069, Verbindung

HRID 2166085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2166085
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:3]=1[C:4]([NH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([F:17])([F:16])[F:15])=[O:5].[C:23](Cl)(Cl)=[O:24].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:3]=1[C:4]1[O:5][C:23](=[O:24])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:15])([F:16])[F:17])[N:6]=1

Komponenten

5

Edukt 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 2811198HCID 2811198, Verbindung

Produkt 1

HCID 23042069HCID 23042069, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2.5 g (7.5 mmol) of 2-chloro-6-fluoro-N'-(α,α,α-trifluoro-o-tolyl)-benzhydrazide are heated to reflux temperature (internal temperature 80° C.) for 16 hours in 35 ml of a 20% solution of phosgene (67 mmol) in toluene. Excess phosgene and toluene are then distilled off, and the residue is dissolved in 30 ml of methylene chloride and heated to reflux temperature for 30 minutes with the addition of 6.7 ml (48 mmol) of triethylamine. The mixture is subsequently washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. After chromatographic purification of the crude product with toluene/n-hexane (1:1) as the eluent and recrystallization from methylene chloride/n-hexane there is obtained pure 5-(2-chloro-6-fluorophenyl)-3-(α,α,α-trifluoro-o-tolyl)-1,3,4-oxadiazol-2(3H)-one, m.p. 109°-109.5° C.; IR spectrum: 1792 cm-1 ; mass spectrum: 358(14), 314(23), 159(100).

Aufarbeitung

  1. distillationExcess phosgene and toluene are then distilled off
  2. dissolutionthe residue is dissolved in 30 ml of methylene chloride
  3. temperatureheated
  4. temperatureto reflux temperature for 30 minutes
  5. washThe mixture is subsequently washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customAfter chromatographic purification of the crude product with toluene/n-hexane (1:1)
  9. customas the eluent and recrystallization from methylene chloride/n-hexane there

Quellen und Nachweise

ORD-Eintrag
ord-9fcac8b1f83a4f22acd9c680dd5d7a13
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04943583

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