Imidazole → HCID 72250843, compound

HRID 2236528Notes

Reaction equation

HRID 2236528 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([OH:14])[CH:6]=1.N1C=CN=C1.[CH:20]([Si:23](Cl)([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])([CH3:22])[CH3:21].C(OCC)(=O)C>CN(C)C=O.CCOCC>[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([O:14][Si:23]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:20]([CH3:22])[CH3:21])[CH:6]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 139400Triisopropylsilyl chlorideHCID 72250763HCID 72250763, compound

Product 1

HCID 72250843HCID 72250843, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

An amount of 3.0 g (15.39 mmol) of 3-hydroxy-4-nitrobenzaldehyde O-methyloxime is stirred in N,N-dimethylformamide (8 mL), followed by addition of imidazole (3.14 g, 46.17 mmol) and 4.89 mL (23.1 mmol) of triisopropylsilyl chloride. The reaction mixture is stirred at room temperature over night. 1:1 ethyl acetate: ether (300 mL) is added and extracted 3× with water, followed by additional washing with brine, dried over magnesium sulfate, evaporated, to afford 5.02 g (93% yield) as a yellow crystals.

Workup

  1. extractionextracted 3× with water
  2. washby additional washing with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto afford 5.02 g (93% yield) as a yellow crystals

Sources & evidence

ORD record
ord-9afc5bee7b90471abf0bd0fd31f186d9
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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