2-(2-Chlorophenoxy)ethanethioamide → HCID 54014773, Verbindung

HRID 1378600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378600
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)Br)=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=1[O:23][CH2:24][C:25]([NH2:27])=[S:26]>C(#N)C.CO>[Cl:20][C:21]1[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=1[O:23][CH2:24][C:25]1[S:26][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:27]=1

Komponenten

5

Edukt 2

HCID 27435522-(2-Chlorophenoxy)ethanethioamideHCID 541605321-(4-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromoethanone

Produkt 1

HCID 54014773HCID 54014773, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1-(4-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone (2.05 g, 6.04 mmol) (Example 1, Step 3) and 2-chlorophenoxy thioacetamide (1.21 g, 6.0 mmol) in 30 mL of acetonitrile was heated to reflux for 3 hours. The solution was diluted with methanol, cooled to 0° C. in an ice bath and a precipitate formed that was removed by filtration. The crude solid was further purified by flash chromatography over silica gel and the appropriate fractions were combined, concentrated in vacuo and crystallized from methanol to provide 2.60 g (98%) of pure 4-2- ((2 -chlorophenoxy) methyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl) thiazole: mp 126°-129° C., 1H NMR (CDCl3) 300 MHz 7.55-7.39 (m, 4H), 7.28-6.90 (m, 8H), 5.44 (s, 2H), 2.49 (s, 3H). 19F NMR (CDCl3) -114.00 (m). Mass spectrum M+H+ =442.

Aufarbeitung

  1. temperatureto reflux for 3 hours
  2. customa precipitate formed
  3. customthat was removed by filtration
  4. customThe crude solid was further purified by flash chromatography over silica gel
  5. concentrationconcentrated in vacuo
  6. customcrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-f90fb59fd7e84caca5fb0bea9679fe43
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668161

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