2-Fluoro-5-methylphenyl isocyanate → 1-[4-(3-Chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea

HRID 871003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871003
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[C:10]([Cl:13])[C:9]=2[C:14]#[N:15])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[N:24]=[C:25]=[O:26]>C1COCC1>[Cl:13][C:10]1[C:9]([C:14]#[N:15])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:25]([NH:24][C:18]3[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=3[F:16])=[O:26])=[CH:7][CH:6]=2)[S:12][N:11]=1

Komponenten

4

Edukt 2

HCID 27333772-Fluoro-5-methylphenyl isocyanate2×HCID 866892235-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile

Produkt 1

HCID 866892241-[4-(3-Chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)ureaAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile (4.565 g, 19.4 mmol) and 2-fluoro-5-methylphenyl isocyanate (5.85 g, 38.7 mmol) in 100 mL of dry THF was heated to reflux overnight. TLC indicated presence of considerable amount of starting material. Additional 2 g of 2-fluoro-5-methylphenyl isocyanate was added and the reaction was continued for another 24 h. The reaction was cooled to RT. THF was removed in vacuo and the resulting solid was stirred in 200 mL of Et2O for 1 h. Product was collected by filtration and washed with Et2O/hexanes to afford a light yellow solid (6.78 g, 90%).

Aufarbeitung

  1. temperatureto reflux overnight
  2. customTHF was removed in vacuo
  3. filtrationProduct was collected by filtration
  4. washwashed with Et2O/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2aaff343e1904d1aa8c5501c749b9629
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969583B2

Notizen zur Reaktion

Wird geladen…