Sodium hydride → 2,2':6',2''-Terpyridine

HRID 1835867Notes

Reaction equation

HRID 1835867 reaction equation
OC[C:3]1[C:4]([C:9]2[C:14](C3C=CC=CN=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.[H-].[Na+]>O1CCOCC1>[CH:8]1[CH:3]=[CH:4][N:5]=[C:6]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([C:4]3[CH:3]=[CH:8][CH:7]=[CH:6][N:5]=3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 131724520HCID 131724520, compound

Product 1

HCID 708482,2':6',2''-Terpyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 0.9 g amount of hydroxymethyl terpyridine tetramer was dissolved in 20 ml of dioxane. Under Argon, 0.12 g of NaH were added and stirred for 15 minutes at room temperature. After adding 0.40 g of epoxide modified silica gel, the temperature was raised to 90° C. for 72 hours. Upon cooling, the mixture was filtered and the silica was washed with a large amount of CH3OH. The product was dried in a vacuum oven at 50° C. for 8 hours. The reaction is shown schematically below:

Workup

  1. temperaturethe temperature was raised to 90° C. for 72 hours
  2. temperatureUpon cooling
  3. filtrationthe mixture was filtered
  4. washthe silica was washed with a large amount of CH3OH
  5. customThe product was dried in a vacuum oven at 50° C. for 8 hours

Sources & evidence

ORD record
ord-d6834cef45f44f8cba055d6e32fc6814
Source dataset
uspto-grants-2004_08
Patent number
US06774082B2

Reaction notes

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