Sodium hydride → HCID 178510937, compound

HRID 1278466Notes

Reaction equation

HRID 1278466 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]#[N:9].[H-].[Na+].Cl.Cl[CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1>CN(C)C=O>[NH:24]1[CH:25]=[C:21]([CH2:20][C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]#[N:9])[N:22]=[CH:23]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 95510alpha-Phenyl-2-pyridineacetonitrileHCID 178478565HCID 178478565, compound

Product 1

HCID 178510937HCID 178510937, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 19.42 g. portion of 2-(2-pyridyl)-2-phenylacetonitrile was stirred with 4.8 g. of 50% sodium hydride in 50 ml. of dimethylformamide, and reacted with 7.65 g. of 4-chloromethylimidazole hydrochloride in 25 ml. of dimethylformamide as described in Example 1. The mixture was stirred at 80°-90° C. for 1 hour, the solvent was removed by evaporation under vacuum, and wthe residue was worked up as described in Example 1 to obtain 11.87 g. of the free base named in the heading above, m.p. 111°-115° C. dec. The product was triturated twice with portions of diethyl ether, and was dissolved in chloroform. The solution was extracted with water and dried over sodium sulfate. Evaporation of the solvent under vacuum gave 11.84 g. of purified free base, m.p. 111°-115° C.

Workup

  1. customthe solvent was removed by evaporation under vacuum
  2. customto obtain 11.87 g
  3. customThe product was triturated twice with portions of diethyl ether
  4. dissolutionwas dissolved in chloroform
  5. extractionThe solution was extracted with water
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent under vacuum
  8. customgave 11.84 g

Sources & evidence

ORD record
ord-3b459b16fbd94425bd4aa6d9e600bf10
Source dataset
uspto-grants-1981_07
Patent number
US04281141

Reaction notes

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