Ethyl Acetate → 2-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]-1,3-benzothiazole-6-carboxamide

HRID 70816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70816
Br[C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[N:33]=[C:34]1[S:38]S[N:36]=[C:35]1Cl)[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:27])([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH2:28][CH3:29])=[O:6].C(OCC)(=O)C>N1C=CC=CC=1.[Cu]I>[C:35]([C:34]1[S:38][C:2]2[CH:3]=[C:4]([C:5]([NH:7][C:8]3[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:27])([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=3[CH2:28][CH3:29])=[O:6])[CH:30]=[CH:31][C:32]=2[N:33]=1)#[N:36]

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 866729733-bromo-4-{[4-chloro-5H-1,2,3-dithiazol-5-ylidene]amino}-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]benzamide

Produkt 1

HCID 866729752-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]-1,3-benzothiazole-6-carboxamideAusbeute 49,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

3-bromo-4-{[4-chloro-5H-1,2,3-dithiazol-5-ylidene]amino}-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]benzamide (0.195 g) and copper(I) iodide (0.057 g) were suspended in pyridine (5 ml), and irradiated(150° C., 20 minutes). After cooling, to the reaction mixture was added ethyl acetate. The mixture was washed with 1N hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The drying agent (anhydrous magnesium sulfate) was removed by filtration and the solvent was distilled off under the reduced pressure. The residue was purified by column chromatography to obtain 2-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]-1,3-benzothiazole-6-carboxamide (0.076 g, 49%).

Aufarbeitung

  1. customirradiated(150° C., 20 minutes)
  2. temperatureAfter cooling, to the reaction mixture
  3. washThe mixture was washed with 1N hydrochloric acid and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe drying agent (anhydrous magnesium sulfate) was removed by filtration
  6. distillationthe solvent was distilled off under the reduced pressure
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c4f0a571843b4dddaee150a7791a0df2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822691B2

Notizen zur Reaktion

Wird geladen…