Pivaloyl chloride → HCID 178429852, Verbindung

HRID 1260362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260362
[CH2:1]=[C:2]1[S:6][C:5](=[NH:7])[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[O:15][C:10]=3[CH:9]=2)[CH2:3]1.CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>C(#N)C.C(Cl)Cl>[CH3:33][C:32]([CH3:35])([CH3:34])[C:31](/[N:7]=[C:5]1\[S:6][C:2]([CH3:1])=[CH:3][N:4]\1[C:8]1[CH:21]=[CH:20][C:11]2[O:12][C:13]([F:19])([F:18])[C:14]([F:16])([F:17])[O:15][C:10]=2[CH:9]=1)=[O:36]

Komponenten

6

Edukt 3

HCID 62493Pivaloyl chloride2×HCID 81531DiisopropylethylamineHCID 866191675-Methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazolidin-2-imine

Produkt 1

HCID 178429852HCID 178429852, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 5-methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazolidin-2-imine (Example 22C, 0.14 g, 0.44 mmol) in acetonitrile (3 mL) was added Hunig's base (0.062 g, 0.48 mmol) followed by pivaloyl chloride (0.064 g, 0.54 mmol). The mixture was heated for 12 hours at 65° C. The mixture was cooled down and more pivaloyl chloride (0.064 g, 0.54 mmol) was added. The mixture was heated again at 65° C. for 12 hours. After cooling, the reaction mixture was diluted with CH2Cl2 (50 mL) and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and dried. After evaporation under reduced pressure, the residue was chromatographed over silica using CH2Cl2-5% MeOH/CH2Cl2 to supply the titled compound. 1H NMR (CDCl3) δ ppm 1.05 (9 H), 2.30 (3 H), 6.80 (1 H), 7.20 (1 H), 7.40 (1 H), 7.50 (1 H); MS (ESI) m/z 405(M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled down
  2. temperatureThe mixture was heated again at 65° C. for 12 hours
  3. temperatureAfter cooling
  4. washwashed with water and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. customdried
  8. customAfter evaporation under reduced pressure
  9. customthe residue was chromatographed over silica

Quellen und Nachweise

ORD-Eintrag
ord-4ffb4775997d4971b6dbff855604e540
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470813B2

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