Acetic Acid → HCID 23447299, compound

HRID 2186126Notes

Reaction equation

HRID 2186126 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[N:8]1([C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)[CH:12]=[CH:11][N:10]=[CH:9]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][CH2:17][C:16]1[CH:15]=[CH:14][C:13]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 89728Aminoacetaldehyde dimethyl acetalHCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23447299HCID 23447299, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethoxyethylamine (526 mg) and 4-(1H-imidazol-1-yl)benzaldehyde (861 mg) in methanol (25 ml) was added acetic acid (600 mg), and the mixture was stirred at room temperature for 1 hour. To the mixture was added, under ice-cooling, sodium triacetoxyborohydride (1.59 g), and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated, and to the residue was added 1 N sodium hydroxide solution. The mixture was extracted with dichloromethane, dried and concentrated to give colorless oil of the title compound (1.21 g).

Workup

  1. additionTo the mixture was added, under ice-
  2. temperaturecooling
  3. concentrationThe reaction solution was concentrated
  4. additionto the residue was added 1 N sodium hydroxide solution
  5. extractionThe mixture was extracted with dichloromethane
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b4b6423c8a084c8a9758fe91d705dc53
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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