2,2,4-Trimethylpentane → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,5-dichlorophenylamino)thiazole

HRID 1378615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378615
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.[Cl:22][C:23]1[CH:24]=[C:25]([NH:30][C:31]([NH2:33])=[S:32])[CH:26]=[C:27]([Cl:29])[CH:28]=1.C(CC(C)(C)C)(C)C>C(O)C.C(OCC)(=O)C.C(Cl)Cl>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:33]=[C:31]([NH:30][C:25]3[CH:24]=[C:23]([Cl:22])[CH:28]=[C:27]([Cl:29])[CH:26]=3)[S:32][C:2]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 109072,2,4-TrimethylpentaneHCID 27375393,5-DichlorophenylthioureaHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Produkt 1

HCID 229121444-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,5-dichlorophenylamino)thiazoleAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.312, 0.841 mmol) in ethanol (10 mL) in a 25 mL round bottom flask was added N-(3,5-dichlorophenyl)thiourea (0.195 g, 0.882 mmol). The solution was heated to reflux (14 hours) and the reaction was cooled to room temperature. The resulting suspension was concentrated in vacuo, suspended in ethyl acetate (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 powdery solid. This solid was dissolved in ethyl acetate/methylene chloride. Addition of isooctane resulted in the precipitation of 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(3,5-dichlorophenylamino)thiazole (0.261 g, 63%) as a pale yellow powder: mp 287°-288° C.; 1HNMR (DMSO d6) 400 mHz 10.84 (s, 1 H), 7.86 (d, J=8.79 Hz, 2 H), 7.73 (s, 2 H), 7.54-7.45 (m, 4 H), 7.22 (t, J=8.79 Hz, 2 H), 7.15 (s, 1 H), 3.22 (s, 3 H); MS m/z 492 (M+). HRMS Δ=4.8 mmu.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux (14 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 powdery solid

Quellen und Nachweise

ORD-Eintrag
ord-8d8550e06b2948dca937c246d6f1e992
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668161

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