Sodium hydride → HCID 14368397, compound

HRID 1762216Notes

Reaction equation

HRID 1762216 reaction equation
[H-].[Na+].[I-].[C:4]([C:6]1[CH:28]=[CH:27][CH:26]=[CH:25][C:7]=1[CH2:8][O:9][C:10]1[C:11]2[N:12]([C:16]([CH2:20][N+](C)(C)C)=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)#[N:5]>C(O)C#C>[C:4]([C:6]1[CH:28]=[CH:27][CH:26]=[CH:25][C:7]=1[CH2:8][O:9][C:10]1[C:11]2[N:12]([C:16]([CH2:20][O:9][CH2:8][C:7]#[CH:6])=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)#[N:5]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 20042512HCID 20042512, compound

Product 1

HCID 14368397HCID 14368397, compoundYield 141.4%

Reagents, catalysts & solvents 1

HCID 7859Propargyl alcoholSolvent

Procedure

To a solution of sodium hydride (60% in mineral oil dispersion, 0.14 g) in 2-propynyl alcohol (6 ml) was added 8-(2-cyanobenzyloxy)-3-trimethylammoniomethyl-2-methylimidazo[1,2-a]pyridine iodide (1.5 g) and the mixture was heated at 90°-95° C. with stirring for 2 hours. After being cooled, the mixture was poured into ice-water and the resulting precipitate was collected by filtration and dissolved in methylene chloride. The solution was treated successively with silica gel (1 g) and activated charcoal and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of methylene chloride and n-hexane to give 8-(2-cyanobenzyloxy)-2-methyl-3-(2-propynyloxymethyl)imidazo[1,2-a]pyridine (0.76 g).

Workup

  1. temperaturethe mixture was heated at 90°-95° C.
  2. temperatureAfter being cooled
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutiondissolved in methylene chloride
  5. additionThe solution was treated successively with silica gel (1 g) and activated charcoal
  6. customevaporated in vacuo
  7. customThe crystalline residue was recrystallized from a mixture of methylene chloride and n-hexane

Sources & evidence

ORD record
ord-ebfbc7935cee4f42a7ea5c701abccd14
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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