Water → HCID 178504697, Verbindung

HRID 2231114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2231114
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([SH:23])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1.C(N(CC)CC)C.O>CC(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([S:23][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 178504698HCID 178504698, Verbindung

Produkt 1

HCID 178504697HCID 178504697, VerbindungAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 4-(4-fluorophenyl)-5-(4-(methylsulfonyl)phenyl]-1H-imidazole-2-thiol (Example 49) (100 mg, 0.29 mmol), 2-chloromethylquinoline hydrochloride (62 mg, 0.29 mmol) and triethylamine (60 mg, 0.58 mmol) in 2-propanol (5 ml) was heated at reflux under an argon atmosphere for 4 hours. The reaction was cooled, poured into water (25 ml) and extracted with ethyl acetate. After drying over sodium sulfate, the solvent was removed and the residue was purified by chromatography on silica gel using 50% ethyl acetate in toluene as the eluent to give 136 mg (85%) of the desired product. Although initially an oil, this material crystallized on standing: mp 179-182° C. Anal. Calc'd. for C26H20N3O2FS2.5H2O (MW 498.60): C, 62.63; H, 4.25; N, 8.43; S, 12.86. Found: C, 62.98; H, 4.43; N, 8.03; S, 12.60.

Aufarbeitung

  1. temperatureat reflux under an argon atmosphere for 4 hours
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying over sodium sulfate
  5. customthe solvent was removed
  6. customthe residue was purified by chromatography on silica gel using 50% ethyl acetate in toluene as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-e381a479f0f648768ecd9b2a98928430
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06426360B1

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