Water → 2-(2-Chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazole

HRID 1378573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378573
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.C(#N)C.[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([NH2:28])=[S:27].O>C(OCC)(=O)C>[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]1[S:27][C:2]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=2)[N:28]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6342AcetonitrileHCID 27348242-ChlorothiobenzamideHCID 53723114HCID 53723114, Verbindung

Produkt 1

HCID 537138882-(2-Chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazoleAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 100 mL one-neck round-bottom flask equipped for magnetic stirring was charged with 2-bromo-2-(4-methylthiophenyl)-1(4-methylphenyl)ethanone from Step 3 (0.300 g, 0.895 mmol) and acetonitrile (20 mL). 2-Chlorothiobenzamide (0.154 g, 0.895 mmol) was added, and the suspension was heated and held at reflux for three hours. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL) and poured into water(50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic solution was dried over MgSO4, filtered and evaporated in vacuo. The residue was purified via flash chromatography (silica gel; 5% ethyl acetate in hexane) to yield 2-(2-chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazole (0.284 g, 78%) as a white solid: mp 125°-126° C. 1H NMR (CDCl3) 300 MHz 8.40(m, 1H), 7.62-7.11(m, 11H), 2.50 (s, 3H), 3.36(s, 3H). Mass spectrum: MH+ =407.

Aufarbeitung

  1. customA 100 mL one-neck round-bottom flask equipped
  2. temperaturethe suspension was heated
  3. temperatureat reflux for three hours
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (2×30 mL)
  6. dry with materialThe combined organic solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified via flash chromatography (silica gel; 5% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5f687ffb93de4f259cda757ddc72fbb4
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668161

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