Acetic Acid → HCID 73197187, compound

HRID 636725

Reaction equation

HRID 636725 reaction equation
[CH3:1][C:2]([N+:5]([O-:7])=O)([CH3:4])[CH3:3].C(O)(=O)C.[N:12]1([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)[CH:16]=[CH:15][N:14]=[CH:13]1>C(O)C.[Zn]>[N:12]1([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[N+:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[O-:7])=[CH:19][CH:18]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 116722-Methyl-2-nitropropaneHCID 7365304-(1H-imidazol-1-yl)benzaldehyde

Product 1

HCID 73197187HCID 73197187, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 1,1-dimethylnitroethane (261.2 mg, 2.53 mmol) and zinc (247.0 mg, 3.78 mmol) in ethanol (3.0 ml) was added acetic acid (451.8 mg, 7.52 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for 30 minutes. After cooling the mixture to 5° C. again, 4-(1-imidazolyl)benzaldehyde (216.5 mg, 1.26 mmol) was added dropwise to the mixture while stirring and stirred at room temperature overnight. Zinc acetate in the mixture was filtered off and the filtrate was concentrated and purified by silica gel chromatography (chloroform/methanol=10/1).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. stirringwhile stirring
  3. stirringstirred at room temperature overnight
  4. filtrationZinc acetate in the mixture was filtered off
  5. concentrationthe filtrate was concentrated
  6. custompurified by silica gel chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-bda5bfc6fee9495a97edd7e3f247ff2e
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Linked notes

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