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Dichloromethane → Flucofuron

HRID 2110087
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2110087
N[C:2]1O[N:5]=[C:4]([C:7]([CH3:10])(C)C)[CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][C:13]=1[C:21]([F:24])([F:23])[F:22].[CH2:25]([Cl:27])Cl>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:20])[NH:5][C:4]2[CH:7]=[CH:10][C:25]([Cl:27])=[C:2]([C:21]([F:24])([F:23])[F:22])[CH:3]=2)=[CH:14][C:13]=1[C:21]([F:22])([F:23])[F:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzene

Produkt 1

HCID 67788Flucofuron

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 5-amino-3-tert-butylisoxazole (0.100 g) in anh toluene (5 mL) was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (0.395 g). The reaction vessel was sealed, heated at 85° C. for 24 h, and cooled to room temp. The reaction mixture was added to a slurry of Dowex® 50WX2-100 resin (0.5 g) in CH2Cl2 (40 mL), and the resulting mixture was stirred vigorously for 72 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (gradient form 100% CH2Cl2 to 5% MeOH/95% CH2Cl2) to give bis(4-chloro-3-(trifluoromethyl)phenyl)urea followed by N-(3-tert-butyl-5-isoxazolyl)-N′-(4-chloro-3-(trifluoromethyl)phenyl)urea. The residue from the symmetrical urea fractions was triturated (Et2O/hexane) to give the urea as a white solid (0.110 g): TLC (3% MeOH/97% CH2Cl2) Rf 0.55; FAB-MS m/z 417 ((M+H)+). C. Urea Interconversions and Misc. Reactions C1. General Method for Alkylation of Hydroxyphenyl Ureas

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperaturecooled to room temp
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (gradient form 100% CH2Cl2 to 5% MeOH/95% CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-3acf076f77fc46edb836d65e9c692f71
Quelldatensatz
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07517880B2

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