Sodium Chloride → Poly(oxy-1,2-ethanediyl), α-methyl-ω-([2,2′:6′,2′′-terpyridin]-4′-yloxy)-

HRID 1030299Notes

Reaction equation

HRID 1030299 reaction equation
[H-].[Na+].CS([C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[N:10]=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:8]=1)(=O)=O.[CH3:25][O:26][CH2:27][CH2:28][OH:29].[Cl-].[Na+]>CN(C=O)C>[CH3:25][O:26][CH2:27][CH2:28][O:29][C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[N:10]=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 12780501HCID 12780501, compound

Product 1

HCID 14879099Poly(oxy-1,2-ethanediyl), α-methyl-ω-([2,2′:6′,2′′-terpyridin]-4′-yloxy)-Yield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% content, oil dispersion, 1.20 g, 0.030 mol) was added to a mixture of 4'-methanesulfonyl-2,2':6',2"-terpyridine (3.11 g, 0.010 mol), 2-methoxyethanol (1.14 g, 0.015 mol) and DMF (0.1 liter) over a period of 10 minutes and then stirred for another 30 minutes. Thereafter, the reaction mixture was refluxed for 3 hours and then cooled to room temperature. The reaction mixture was then poured into an aqueous 4M sodium chloride solution and the crystal that precipitated was taken out by filtration under suction and then washed with water and hexane The crystal thus taken out was purified by passing the same into an alumina column using chloroform as an eluent, whereby 2.92 g of the above-entitled product (T-7) was obtained. Yield: 95%. m.p. 105.0 to 105.5° C.

Workup

  1. temperatureThereafter, the reaction mixture was refluxed for 3 hours
  2. customthe crystal that precipitated
  3. filtrationwas taken out by filtration under suction
  4. washwashed with water and hexane The crystal
  5. customthus taken out was purified

Sources & evidence

ORD record
ord-280f971984e647f3b4cbb80b4cfa8b08
Source dataset
uspto-grants-1992_04
Patent number
US05104988

Reaction notes

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