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Triethylamine → 3-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-tert-butyl-2,3-dihydro-1,3,4-oxadiazole-2-one

HRID 893314
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 893314
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[NH:24][NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].C(N(CC)CC)C>>[CH3:29][C:27]([C:26]1[O:31][C:1](=[O:2])[N:24]([C:14]2[C:13]([Cl:12])=[CH:18][C:17]([C:19]([F:20])([F:22])[F:21])=[CH:16][C:15]=2[Cl:23])[N:25]=1)([CH3:28])[CH3:30]
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Komponenten

4

Edukt 3

HCID 8471TriethylamineHCID 15279907N'-(2,6-dichloro-4-trifluoromethylphenyl)-2,2-dimethylpropionhydrazideHCID 19083224Phosgen toluene

Produkt 1

HCID 198922363-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-tert-butyl-2,3-dihydro-1,3,4-oxadiazole-2-oneAusbeute 45,1 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In 4.6 ml (8.9 mmols) of 20% phosgene-toluene solution, 0.33 g (1 mmol) of N'-(2,6-dichloro-4-trifluoromethylphenyl)-2,2-dimethylpropionhydrazide was heated to reflux for 16 hours (inner temperature of 80° C.). Then, an excess of phosgene and toluene was distilled off. After the residue was dissolved in 5 ml of methylene chloride, 0.65 g (6.4 mmols) of triethylamine was added to the solution and the mixture was heated to reflux for 30 minutes. Next, the mixture was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The thus obtained crude product was subjected to silica gel column chromatography to give 0.16 g of 5-(1,1-dimethylethyl)-3-(2,6-dichloro-4-trifluoromethylphenyl)-1,3,4-oxadiazolin-2-one.

Aufarbeitung

  1. distillationThen, an excess of phosgene and toluene was distilled off
  2. dissolutionAfter the residue was dissolved in 5 ml of methylene chloride
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 30 minutes
  5. washNext, the mixture was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe thus obtained crude product

Quellen und Nachweise

ORD-Eintrag
ord-ab1524075eee422fb0525349ba4269b8
Quelldatensatz
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05124341

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