Water → 4-[4-(4-Imidazol-1-yl-butyl)-phenoxymethyl]-2-[2-(4-trifluoromethane-sulfinyl-phenyl)-vinyl]-oxazole

HRID 750943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 750943
[H-].[Na+].[N:3]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH2:20][C:21]1[N:22]=[C:23]([CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([S:34]([C:36]([F:39])([F:38])[F:37])=[O:35])=[CH:30][CH:29]=2)[O:24][CH:25]=1.O>CN(C=O)C>[N:3]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:20][C:21]3[N:22]=[C:23]([CH:26]=[CH:27][C:28]4[CH:29]=[CH:30][C:31]([S:34]([C:36]([F:39])([F:37])[F:38])=[O:35])=[CH:32][CH:33]=4)[O:24][CH:25]=3)=[CH:16][CH:17]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 220096641-[4-(4-Hydroxyphenyl)butyl]imidazoleHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole

Produkt 1

HCID 692901934-[4-(4-Imidazol-1-yl-butyl)-phenoxymethyl]-2-[2-(4-trifluoromethane-sulfinyl-phenyl)-vinyl]-oxazoleAusbeute 64,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

13.0 mg (0.50 mmol) 95% sodium hydride were given to a solution of 108 mg (0.50 mmol) 4-(4-Imidazol-1-yl-butyl)-phenol in 4.0 ml DMF and stirred for 15 min. 168 mg (0.50 mmol) 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole were added and stirring continued overnight. After addition of 10 ml water the resulting precipitate was washed with water, 10 ml methanol/water 1:1 and with diethyl ether. The residue was purified by chromatography on silica gel (eluent: ethyl acetate/methanol 9:1) to yield 167 mg colorless powder that was further purified by HPLC-MS to give 75 mg (29%) colorless powder.

Aufarbeitung

  1. stirringstirring continued overnight
  2. washwas washed with water, 10 ml methanol/water 1:1 and with diethyl ether
  3. customThe residue was purified by chromatography on silica gel (eluent: ethyl acetate/methanol 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-c38c58a721a54cd396ba376c16f471bb
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405231B2

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