Dimethylformamide → 4-Chloro-2-ethyl-5-[4-(trifluoromethyl)phenyl]isothiazol-3(2H)-one 1,1-dioxide

HRID 729253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729253
[C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].[CH2:7]([N:9]1C(=O)C(O)=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[S:10]1(=[O:27])=[O:26])[CH3:8].CN(C=O)C>C(Cl)Cl>[Cl:6][C:1]1[C:2](=[O:3])[N:9]([CH2:7][CH3:8])[S:10](=[O:27])(=[O:26])[C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 68661688HCID 68661688, Verbindung

Produkt 1

HCID 686618714-Chloro-2-ethyl-5-[4-(trifluoromethyl)phenyl]isothiazol-3(2H)-one 1,1-dioxideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Oxalyl chloride (0.379 g, 2.99 mmol) was added dropwise to a solution of 2-ethyl-4-hydroxy-5-[4-(trifluoromethyl)phenyl]isothiazol-3(2H)-one 1,1-dioxide (0.480 g, 1.49 mmol) and DMF (0.109 g, 1.49 mmol) in DCM (12 mL). The mixture was refluxed for 1 h. It was evaporated and water was added. The resulting mixture was extracted with EtOAc, and the combined organic layers were washed with brine and evaporated to give the title compound (0.306 g, 71%) as a solid; 1H NMR (500 MHz, DMSO-d6): δ 8.07-8.11 (m, 4H), 3.81 (q, 2H), 1.33 (t, 3H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 h
  2. customIt was evaporated
  3. additionwater was added
  4. extractionThe resulting mixture was extracted with EtOAc
  5. washthe combined organic layers were washed with brine
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-97cca3e7a7af49b5a7379c80f8dbe2a3
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582629B2

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