Sodium hydride → HCID 21848878, compound

HRID 1464267Notes

Reaction equation

HRID 1464267 reaction equation
[H-].[Na+].[C:3]([NH:5][C:6](=[N:8][CH3:9])[CH3:7])#[N:4].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]Cl)=[CH:13][N:12]=1>CN(C)C=O>[C:3]([N:5]([CH2:17][C:14]1[CH:15]=[CH:16][C:11]([Cl:10])=[N:12][CH:13]=1)[C:6](=[N:8][CH3:9])[CH3:7])#[N:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 15300768(1E)-N-Cyano-N′-methylethanimidamide

Product 1

HCID 21848878HCID 21848878, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.6 g of sodium hydride (purity 60%) was added to the solution of 1.3 g of N-cyano-N'-methylacetamidine in 20 ml of N,N-dimethylformamide at ice bath temperature. After stirring it at the same temperature for 1 hour, 2.2 g of 2-chloro-5-pyridylmethylchloride was added to the mixture, followed by stirring for 5 hours at room temperature. The reaction mixture was then poured into ice-water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was purified by column chromatography on silica gel to afford 1.5 g of compound No. 22 m.p. 101°-103° C.

Workup

  1. stirringby stirring for 5 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-16c75e4fece343bab60ec673ecd15854
Source dataset
uspto-grants-1994_04
Patent number
US05304566

Reaction notes

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