2,6-Difluorobenzoyl isocyanate → 1-[3-Chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl)urea

HRID 37321

Reaktionsgleichung

Reaktionsgleichung von HRID 37321
[Cl:1][C:2]1[C:3]([CH3:22])=[C:4]([CH:6]=[C:7]([CH3:21])[C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([Cl:20])=[CH:12][CH:11]=1)[NH2:5].[F:23][C:24]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:25]=1[C:26]([N:28]=[C:29]=[O:30])=[O:27]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH3:22])=[C:4]([NH:5][C:29]([NH:28][C:26](=[O:27])[C:25]2[C:31]([F:35])=[CH:32][CH:33]=[CH:34][C:24]=2[F:23])=[O:30])[CH:6]=[C:7]([CH3:21])[C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([Cl:20])=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 132460063-Chloro-4-[(4-chloronaphthalen-1-yl)oxy]-2,5-dimethylaniline

Produkt 1

HCID 132621271-[3-Chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl)ureaAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Into a solution containing 3.0 grams (9.0 mmol) of 3-chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethylaniline prepared in Part B of Example I in 25 milliliters of toluene which solution was warmed to a temperature of 50° C. and placed under a nitrogen atmosphere was slowly added a solution containing 2.5 grams (13.5 mmol) of 2,6-difluorobenzoyl isocyanate in 5 milliters of toluene. After stirring for one hour at a temperature of 50° C. the reaction mixture was cooled to room temperature, placed in an ice bath, and filtered through a Buchner funnel. The collected solid was dried under a vacuum at a temperature of 50° C. to afford 2.89 grams of 1-[3-chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethylphenyl]-3-(2.6-difluorobenzoyl)urea as a white powder havin a melting point of 187° C. Elemental analysis of the white powder indicated the following:

Aufarbeitung

  1. additionwas slowly added a solution
  2. temperaturewas cooled to room temperature
  3. customplaced in an ice bath
  4. filtrationfiltered through a Buchner funnel
  5. customThe collected solid was dried under a vacuum at a temperature of 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-57899e87306849a6a6e8ba027709c95b
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420163

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