Sodium Hydroxide → HCID 178436222, Verbindung

HRID 991595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991595
[NH2:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:12]([C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[C:15]=1[CH:16]=O)[CH3:13].[BH3-]C#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH2:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:14]([CH2:12][CH3:13])[C:15]=1[CH2:16][NH:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:23]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 131847782,6-DiethylbenzaldehydeHCID 178432166HCID 178432166, Verbindung

Produkt 1

HCID 178436222HCID 178436222, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

4-Amino-2-methylbenzimidazole (0.79 g, 5.4 mmol) and 2,6-diethylbenzaldehyde (1.1 g, 6.6 mmol) were dissolved in methanol (30 ml). ZnCl2 (0.9 g, 6.6 mmol) and subsequently NaBH3CN (0.42 g, 6.6 mmol) in small portions were added and the mixture was refluxed under argon for 3 hours and was stirred at room temperature for 16 h. The mixture was poured over an aqueous 1M NaOH solution (50 ml). The resultant yellow suspension was extracted with DCM and the organic solution was washed with brine, dried over Na2SO4 and then evaporated under reduced pressure. The oily residue (1.8 g) was purified by crystallization from a mixture of ethyl acetate and acetonitrile to give 0.65 g (41%) of the title compound.

Aufarbeitung

  1. temperaturethe mixture was refluxed under argon for 3 hours
  2. extractionThe resultant yellow suspension was extracted with DCM
  3. washthe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe oily residue (1.8 g) was purified by crystallization from a mixture of ethyl acetate and acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-4455fb3659784a0da15e42715ebbaf7f
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465505B1

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