Water → HCID 58654363, Verbindung

HRID 1170488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1170488
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[H-].[Na+].Cl[C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)[N:25]=1.O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)[N:25]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 229583304-Chloro-2-(1H-imidazol-1-yl)-6-methylpyrimidine

Produkt 1

HCID 58654363HCID 58654363, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

To a solution of (benzhydrylidene-amino)-acetic acid ethyl ester (2.67 g, 10.0 mmol) in DMSO (50 mL) was added NaH (600 mg of a 60% dispersion on mineral oil, 15.0 mmol) slowly at r.t. under nitrogen and the mixture was stirred for 5 min. Then a solution of 4-chloro-2-imidazol-1-yl-6-methyl-pyrimidine (1.95 g, 10.0 mmol) in DMSO (15 mL) was added and the reaction mixture stirred at r.t overnight. Water was added and the solution was extracted with ethyl acetate, washed with brine and dried over Na2SO4. Evaporation of the solvent gave residue which was purified by column chromatography to give 1.30 g (31%) of (benzhydrylidene-amino)-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-acetic acid ethyl ester. [M+H]+ 426.18.

Aufarbeitung

  1. stirringthe reaction mixture stirred at r.t overnight
  2. extractionthe solution was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent
  6. customgave residue which
  7. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-454abbfa41474606b60f0fd8d288ab20
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825256B2

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