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Cesium carbonate → HCID 86585865, Verbindung

HRID 1246841
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1246841
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N+:11]([O-:14])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].[C:19](=O)([O-])[O-].[Cs+].[Cs+].C([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[SH:34])(C)C.[CH3:35][C:36](N(C)C)=O>>[CH:36]([C:4]1[C:3]([C:15]([F:18])([F:17])[F:16])=[C:2]([S:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:28]=2)[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][N+:11]([O-:14])=[CH:10][CH:9]=1)([CH3:35])[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 96003Benzenethiol, 2-(1-methylethyl)-HCID 21906801Pyridine, 4-[4-fluoro-3-(trifluoromethyl)phenyl]-, 1-oxide

Produkt 1

HCID 86585865HCID 86585865, VerbindungAusbeute 84 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Then, 4-(4-(2-isopropyl-phenylsulfanyl-3-trifluoromethyl-phenyl)-pyridine-1-oxide 75 was prepared as follows. A solution of compound 74 (2.51 g, 9.76 mmol) in dimethylacetamide (100 mL) was purged with nitrogen gas for 10 minutes. To it was added cesium carbonate (3.80 g, 11.7 mmol), followed by 2-isopropylthiophenol (4.90 mL, 29.3 mmol). The reaction was heated at 100° C. for 16 hours. The mixture was partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was separated, washed with brine (5×200 mL), dried over MgSO4 and then filtered. After evaporating the solvent, the crude material was loaded to a silica gel column, eluting with 10% methanol in ethyl acetate to give a white solid 75 (3.19 g 84%). 1H-NMR (CDCl3, 400 MHz) δ 1.19 (d, J=6.8 Hz, 6H), 3.51 (heptaplet, J=6.8 Hz, 1H), 6.90 (d, J=8.1 Hz, 1H), 7.22–7.28 (m, 1H), 7.44–7.51 (m, 6H), 7.84 (d, J=2.1 Hz, 1H), 8.24 (d, J=7.4 Hz, 2H); MS (DCI) m/z 390 (M+H)+.

Aufarbeitung

  1. customThen, 4-(4-(2-isopropyl-phenylsulfanyl-3-trifluoromethyl-phenyl)-pyridine-1-oxide 75 was prepared
  2. customThe mixture was partitioned between ethyl acetate (200 mL) and water (200 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (5×200 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customAfter evaporating the solvent
  8. washeluting with 10% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0488876098504056bad3ba0d51145aaa
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07129247B2

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