Sodium Hydroxide → HCID 24952866, compound

HRID 1946965Notes

Reaction equation

HRID 1946965 reaction equation
[CH3:1][C:2]1[N:3](O)[C:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][N:6]=1.C(=O)(O)[O-].[Na+].[OH-].[Na+]>CO>[CH3:1][C:2]1[NH:3][C:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59742747HCID 59742747, compound

Product 1

HCID 24952866HCID 24952866, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-5-phenethyl-imidazol-1-ol (0.20 g, 1.0 mmol) in methanol (3.5 ml) titanium(III)-chloride solution (2.5 ml, 15%) was added and the mixture was stirred overnight at room temperature. First saturated sodium bicarbonate solution then diluted sodium hydroxide solution was added to achieve a basic pH. The mixture was extracted twice with dichloromethane, the combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by column chromatography (dichloromethane/methanol=9:1) to yield a white solid (0.14 mg, 75%); MS (EI): 186.1 (M+).

Workup

  1. extractionThe mixture was extracted twice with dichloromethane
  2. dry with materialthe combined organic layers were dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by column chromatography (dichloromethane/methanol=9:1)

Sources & evidence

ORD record
ord-39b8e639ae594ac4b02e8c3eae399b0e
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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