Ammonium Chloride → 4-[4-(p-tert-Butylaminocarbonylphenyl)-4-hydroxy-n-butyl]-1-trimethylsilylimidazole

HRID 477970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477970
[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH:20]([CH2:22][CH2:23][CH2:24][C:25]1[N:26]=[CH:27][N:28]([Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:29]=1)=[O:21].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:20]([OH:21])[CH2:22][CH2:23][CH2:24][C:25]2[N:26]=[CH:27][N:28]([Si:30]([CH3:31])([CH3:32])[CH3:33])[CH:29]=2)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 6032584-bromo-N-tert-butylbenzamideHCID 199304284-(3-Formyl-n-propyl)-1-trimethylsilylimidazoleHCID 178418339Butyllithium

Produkt 1

HCID 199304194-[4-(p-tert-Butylaminocarbonylphenyl)-4-hydroxy-n-butyl]-1-trimethylsilylimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 6.95 g of p-(tert-butylaminocarbonyl)-bromobenzene is dissolved in 175 ml of tetrahydrofuran at -70° under nitrogen and 20.1 ml of a solution of n-butyllithium (2.7M) in hexane is added dropwise. After reacting 30 min, a solution of 5.69 g of 4-(3-formyl-n-propyl)-1-trimethylsilylimidazole in 10 ml of tetrahydrofuran is added slowly. The reaction mixture is allowed to warm slowly to room temperature and 20 ml of ammonium chloride is added. The organic layer is separated, dried over sodium sulfate and evaporated to yield the title compound (b).

Aufarbeitung

  1. customThe organic layer is separated
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c90f12d3ba3d4c29b6ef22c6f07642cd
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889861

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