Hydrogen Peroxide → HCID 58015512, compound

HRID 219285Notes

Reaction equation

HRID 219285 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]([C:14]#[C:15][Si](C)(C)C)=[C:10]([CH:13]=1)[C:11]#[N:12].C(=O)([O-])[O-:21].[Na+].[Na+].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O.CO>[NH4+:8].[OH-:2].[C:14]([C:9]1[N:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:13][C:10]=1[C:11]([NH2:12])=[O:21])#[CH:15]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 58015479HCID 58015479, compound

Product 2

HCID 14923Ammonium HydroxideYield 1%HCID 58015512HCID 58015512, compoundYield 121.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

5-(2-methoxyethoxy)-2-(2-(trimethylsilyl)ethynyl)nicotinonitrile (4.23 g, 15 mmol) was dissolved in acetone (60 mL). To the solution was added 3 M sodium carbonate (62 ml, 185 mmol) and hydrogen peroxide (31 ml, 308 mmol) dropwise, and it was stirred at room temperature for 4 h. After completion, the reaction was cooled to 0° C. and to it was slowly added sodium thiosulfate (200 mL) with stirring. The aqueous layer was extracted with DCM (×3, 200 mL), and the combined organics were concentrated and purified via MPLC eluting with 100% DCM to 90% DCM:10% MeOH:1% NH4OH to yield 2-ethynyl-5-(2-methoxyethoxy)nicotinamide (2.0 g, 59% yield).

Workup

  1. temperatureAfter completion, the reaction was cooled to 0° C. and to it
  2. stirringwith stirring
  3. extractionThe aqueous layer was extracted with DCM (×3, 200 mL)
  4. concentrationthe combined organics were concentrated
  5. custompurified via MPLC
  6. washeluting with 100% DCM to 90% DCM

Sources & evidence

ORD record
ord-d4ee38bb634e4d21ab7e3aa71c4837ed
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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