Triethylamine → Trifludimoxazin

HRID 405686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405686
CNC(NC)=[S:4].C(N(CC)CC)C.[F:14][C:15]1([F:33])[O:20][C:19]2[CH:21]=[C:22]([F:28])[C:23]([N:25]=[C:26]=[O:27])=[CH:24][C:18]=2[N:17]([CH2:29][C:30]#[CH:31])[C:16]1=[O:32].[C:34](N1C=CN=C1)([N:36]1[CH:40]=[CH:39][N:38]=[CH:37]1)=[O:35]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:39][N:38]1[C:37](=[S:4])[N:36]([CH3:40])[C:34](=[O:35])[N:25]([C:23]2[C:22]([F:28])=[CH:21][C:19]3[O:20][C:15]([F:14])([F:33])[C:16](=[O:32])[N:17]([CH2:29][C:30]#[CH:31])[C:18]=3[CH:24]=2)[C:26]1=[O:27]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2723631N,N'-DimethylthioureaHCID 866643002,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Produkt 1

HCID 49831143Trifludimoxazin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 22728543Water ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 1,3-dimethylthiourea (2.489 g, 23.89 mmol) and triethylamine (2.78 ml, 19.91 mmol) in dry toluene was added 2,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (5.62 g, 19.91 mmol) in dry toluene. Hereto was subsequently added carbonyldiimidazole (CDI; 6.46 g, 39.8 mmol) and the resulting mixture was stirred at 80° C. overnight. Then the reaction mixture was cooled to room temperature and poured into ethyl acetate/water under stirring. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined extracts were washed with brine, dried with Na2SO4 and concentrated to yield 14.4 g.

Aufarbeitung

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. stirringunder stirring
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined extracts were washed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customto yield 14.4 g

Quellen und Nachweise

ORD-Eintrag
ord-dad3d3b56d2343c5b9ec6f5b7e1c341f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754008B2

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