N-bromobutanimide → ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate

HRID 216608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216608
[Br:1]N1C(=O)CCC1=O.[C:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([N:21]2[CH:25]=[CH:24][N:23]=[C:22]2[S:26][C:27]([F:34])([F:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:13][CH:12]=1)#[N:10]>ClCCl>[Br:1][C:25]1[N:21]([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]([C:9]#[N:10])=[CH:12][CH:13]=2)[C:22]([S:26][C:27]([F:34])([F:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:23][CH:24]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 59225900ethyl 2-(1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate

Produkt 1

HCID 59225861ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-bromosuccinimide (1 eq) was added in three portions to a solution of ethyl 2-(1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate (1 eq) in dichloromethane at 0° C. and then stirred at room temperature for 18 h. The mixture was washed twice with water and once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-50% ethyl acetate/hexanes) provided ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate.

Aufarbeitung

  1. washThe mixture was washed twice with water and once with saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (0-50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e94574e3e752415d99d2ab964b3148ef
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193234B2

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