Acetaldehyde → HCID 68762714, Verbindung

HRID 1398936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398936
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][OH:23])[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[OH:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:24](=O)[CH3:25].[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:28].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+].O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH:11]([OH:12])[C:9]1[N:8]([CH2:21][CH2:22][OH:23])[C:7]2[C:2]([N:1]([CH2:24][CH3:25])[CH2:27][CH3:28])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Komponenten

8

Edukt 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68762744HCID 68762744, Verbindung

Produkt 1

HCID 68762714HCID 68762714, VerbindungAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 2-{7-amino-2-[(2,4-dichlorophenyl)(hydroxy)methyl]-1H-benzimidazol-1-yl}ethanol (7.58 g, 21.5 mmol) in methanol (220 mL) and acetic acid (11 mL) was added acetoaldehyde (8.04 mL, 129 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (27.3 g, 129 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 2 h, the mixture was diluted with aqueous sodium hydrogen carbonate and water, and extracted with ethyl acetate. The combined organic layer was washed with 1N aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to afford a crude solid, which was washed with diisopropylether to give the title compound as a colorless solid (8.70 g, 21.3 mmol, 99%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with 1N aqueous sodium hydroxide and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate
  7. customto afford a crude solid, which
  8. washwas washed with diisopropylether

Quellen und Nachweise

ORD-Eintrag
ord-29e4630ddd2c466dab774c5d00499cf6
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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