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

HRID 37323
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 37323
[CH3:1][C:2]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[C:11]([CH3:12])=[CH:10][C:8]([NH2:9])=[C:7]([CH3:13])[C:6]=1[Cl:14].[F:20][C:21]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:22]=1[C:23]([N:25]=[C:26]=[O:27])=[O:24]>C1(C)C=CC=CC=1.CCCCCC>[Cl:14][C:6]1[C:7]([CH3:13])=[C:8]([NH:9][C:26]([NH:25][C:23](=[O:24])[C:22]2[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:21]=2[F:20])=[O:27])[CH:10]=[C:11]([CH3:12])[C:5]=1[O:4][C:3]1[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:2]=1[CH3:1]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 148206063-Chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylaniline

Produkt 1

HCID 146260521-[3-Chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl)-urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8058Hexane
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Into a solution of 4-(2,4-dimethylphenoxy)-2,5-dimethyl-3-chloroaniline (1.75 grams, 6.3 mmol) prepared in Part B in 7 milliliters of toluene, which solution was warmed to a temperature of 50° C., was added 1.14 grams (6.2 mmol) of 2,6-difluorobenzoyl isocyanate in 1.5 milliliters of toluene. The reaction mixture was heated to a temperature of 90° C. and maintained at this temperature for 0.5 hours. After cooling to room temperature, the reaction mixture was diluted with 20 milliliters of hexane and then cooled in an ice bath. A precipitate formed which was collected by filtration and washed with a cold solution of 50% hexane in toluene. After vacuum drying, a white solid (1.26 grams) which was identified as 1-[3-chloro-4-(2,4-dimethylphenoxy)-2,5-dimethylphenyl]-3-(2,6-difluorobenzoyl)urea was obtained having a melting point of 183° C.-185° C. Elemental analysis of the white solid indicated the following:

Aufarbeitung

  1. temperatureThe reaction mixture was heated to a temperature of 90° C.
  2. temperaturemaintained at this temperature for 0.5 hours
  3. temperatureAfter cooling to room temperature
  4. temperaturecooled in an ice bath
  5. customA precipitate formed which
  6. filtrationwas collected by filtration
  7. washwashed with a cold solution of 50% hexane in toluene
  8. customAfter vacuum drying
  9. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-18c1782e1b304e80ae3a4d9b3612cd5f
Quelldatensatz
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05420163

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