Acetaldehyde → HCID 68762714, compound

HRID 1398936Notes

Reaction equation

HRID 1398936 reaction equation
[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

Participants

8

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68762744HCID 68762744, compound

Product 1

HCID 68762714HCID 68762714, compoundYield 99.1%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-29e4630ddd2c466dab774c5d00499cf6
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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