Water → {2-(3-Ethoxy-4-(2-methoxyethoxy)phenyl]-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

HRID 1698733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698733
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][O:10][CH3:11].[CH3:12][O:13][C:14](=[O:43])[N:15]=[C:16]([S:41][CH3:42])[C:17]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([O:38][CH2:39][CH3:40])[CH:32]=1)=[N:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:29]=[C:28]([CH3:30])[O:27][N:26]=2)=[CH:21][CH:20]=1.O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(OCC)(=O)C>[CH3:12][O:13][C:14](=[O:43])[N:15]=[C:16]([S:41][CH3:42])[C:17]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:8][CH2:9][O:10][CH3:11])=[C:33]([O:38][CH2:39][CH3:40])[CH:32]=1)=[N:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:29]=[C:28]([CH3:30])[O:27][N:26]=2)=[CH:21][CH:20]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 136366385{2-(3-Ethoxy-4-hydroxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

Produkt 1

HCID 72312845{2-(3-Ethoxy-4-(2-methoxyethoxy)phenyl]-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After adding 200 mg of potassium carbonate, 10 mg of tetrabutylammonium iodide and 200 mg of 1-bromo-2-methoxyethane to a solution of {2-(3-ethoxy-4-hydroxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example 126a) in 1 ml of DMF, the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, extraction was performed with ethyl acetate, and the organic layers were combined and washed with 0.5 N hydrochloric acid and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (193 mg) as a yellow solid.

Aufarbeitung

  1. washwashed with 0.5 N hydrochloric acid and saturated brine in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-1b1d03e62ada4692880c4e1955d643d2
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163787B2

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