Ethylthiourea → 2-Ethylamino-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)thiazole

HRID 1378613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378613
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[CH2:22]([NH:24][C:25]([NH2:27])=[S:26])[CH3:23]>C(O)C>[CH2:22]([NH:24][C:25]1[S:26][C:2]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[N:27]=1)[CH3:23]

Komponenten

4

Edukt 2

HCID 3032338EthylthioureaHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Produkt 1

HCID 229117462-Ethylamino-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)thiazoleAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.405 g, 1.09 mmol) in ethanol (10 mL) in a 25 mL round bottom flask was added N-ethylthiourea (0.114 g, 1.09 mmol) and the solution was heated to reflux for 14 hours. The reaction was cooled to room temperature and the resulting suspension was concentrated in vacuo, suspended in methylene chloride (100 mL) and washed with NaHCO3 saturated solution (3×10 mL), sodium carbonate solution (10%, 3×20 mL), dried over sodium sulfate, filtered and concentrated. The crude product was recrystallized from methylene chloride and isooctane yielding 2-ethylamino-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)thiazole (0.218 g, 53%) as a white powdery crystals: mp 218°-219° C., 1HNMR (DMSO d6) 400 mHz 7.94 (t, 5.38 Hz, 1 H), 7.78 (d, J=8.56 Hz, 2 H), 7.45-7.40 (m, 2 H), 7.37 (d, J=8.56 Hz, 2 H), 7.15 (t, J=9.05 Hz, 2 H), 3.31 (q, J=7.10 Hz, 2 H), 3.18 (s, 3 H), 1.18 (t, J=7.10 Hz, 3 H); MS m/z 377 (M+H). HRMS Δ=0.5 mmu.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureto reflux for 14 hours
  3. concentrationthe resulting suspension was concentrated in vacuo
  4. washwashed with NaHCO3 saturated solution (3×10 mL), sodium carbonate solution (10%, 3×20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was recrystallized from methylene chloride and isooctane

Quellen und Nachweise

ORD-Eintrag
ord-0362e441824a4ef2aecfbf661c0c69af
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668161

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