Dichloromethane → HCID 54412494, Verbindung

HRID 1378580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378580
Br[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=O.[C:20]([NH2:23])(=[S:22])[CH3:21].C(Cl)Cl.CCCCCC>C(O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:2]2[S:22][C:20]([CH3:21])=[N:23][C:3]=2[C:5]2[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 2723949ThioacetamideHCID 54373829HCID 54373829, Verbindung

Produkt 1

HCID 54412494HCID 54412494, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-2-(4-fluorophenyl)-1-(4-methylthiophenyl) ethanone from Step 2 (0.70 g, 2.10 mmol) in ethanol (20 mL) in a 50 mL round bottom flask was added thioacetamide (0.16 g, 2.10 mmol) and the mixture heated to reflux for 20 hours. The reaction was cooled to room temperature and concentrated in vacuo and dissolved in methylene chloride. This solution was washed with NaHCO3 saturated solution and dried over Na2SO4, filtered and reconcentrated in vacuo yielding a white crystalline solid. Flash chromatography of this solid (2:1 methylene chloride: hexane) yielded 5-(4-fluorophenyl)-4-(4-methylthiophenyl) -2-methylthiazole as a white solid (0.45 g, 68%): mp 104°-105° C. 1H NMR (CDCl3) 400 mHz δ7.39 (d, J=8.32, 2H), 7.28 (dd, J=8.80, 5.14, 2H), 7.15 (d, J=8.32, 2H), 7.00 (t, J=8.80, 2H), 2.74 (s, 3H), 2.47 (s, 3H). MS (EI): m/z 316 (M+H). HRMS Δ=0.000 mmu.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux for 20 hours
  3. concentrationconcentrated in vacuo
  4. dissolutiondissolved in methylene chloride
  5. washThis solution was washed with NaHCO3 saturated solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customyielding a white crystalline solid

Quellen und Nachweise

ORD-Eintrag
ord-b77f595f1e0f4677a732f530a2e27cf2
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668161

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