(4-Cyanophenyl)thiourea → HCID 22911871, Verbindung

HRID 1378616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378616
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.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[S:32])=[CH:26][CH:25]=1)#[N:23]>C(O)C>[C:22]([C:24]1[CH:25]=[CH:26][C:27]([NH:30][C:31]2[S:32][C:2]([C:12]3[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=3)=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=3)[N:33]=2)=[CH:28][CH:29]=1)#[N:23]

Komponenten

4

Edukt 2

HCID 2757973(4-Cyanophenyl)thioureaHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Produkt 1

HCID 22911871HCID 22911871, VerbindungAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.413, 1.11 mmol) in ethanol (10 mL) in a 25 mL round bottom flask was added N-(4-cyanophenyl)thiourea (0.207 g, 1.17 mmol). The solution was heated to reflux (24 hours) and the reaction was cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in methylene chloride (100 mL) and washed with sodium carbonate solution (10%, 3×20 mL), brine (1×20 mL), dried over sodium sulfate, filtered and concentrated yielding a solid. This solid was flash chromatographed (1:1, hexane:ethyl acetate with 1% acetic acid). The resulting product was recrystallized from methylene chloride and isooctane yielding 2-(4-cyanophenylamino)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)thiazole (0.266 g, 53%) as a pale yellow solid: mp 273°-274° C.; 1HNMR (DMSO d6) 400 mHz 10.98 (s, 1 H), 7.86 (d, J=8.32 Hz, 2 H), 7.83 (d, J=9.05 Hz, 2 H), 7.76 (d, J=8.80 Hz, 2 H), 7.55-7.47 (m, 4 H), 7.21 (t, J=8.80 Hz, 2 H), 3.22 (s, 3 H); MS m/z 450 (M+H). HRMS Δ=2.6 mmu.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux (24 hours)
  3. concentrationThe resulting suspension was concentrated in vacuo
  4. washwashed with sodium carbonate solution (10%, 3×20 mL), brine (1×20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customyielding a solid
  9. customchromatographed (1:1, hexane:ethyl acetate with 1% acetic acid)
  10. customThe resulting product was recrystallized from methylene chloride and isooctane

Quellen und Nachweise

ORD-Eintrag
ord-baa7ab97b3074ef7a721894855400b83
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668161

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