Acetic Acid → HCID 23447299, compound

HRID 1840538Notes

Reaction equation

HRID 1840538 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-b7f8eb6baafb4728a2e9b9060c90f0ca
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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