Dimethylformamide → HCID 22314805, compound

HRID 1634038Notes

Reaction equation

HRID 1634038 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#N)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13]I.C[N:16]([CH:18]=[O:19])C>>[ClH:1].[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]([CH3:9])([CH3:13])[C:18]([NH2:16])=[O:19])[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 123966084-Pyridylacetonitrile hydrochloride

Product 1

HCID 22314805HCID 22314805, compound

Conditions

Temperature
0 °C

Procedure

A mixture of 3 g of pyridin-4-ylacetonitrile hydrochloride in 50 ml of DMF is cooled to 0° C., 2.6 g of 60% sodium hydride in oil are added in small portions and the mixture is left stirring for 2 hours at RT. The reaction mixture is cooled on an ice bath, 6 g of methyl iodide are added dropwise and the mixture is left stirring overnight at RT. The reaction mixture is poured over a water/ice mixture, extracted with ether, the organic phase washed with a saturated NaCl solution, dried over MgSO4, filtered and the solvent evaporated off under vacuum. The residue is chromatographed on H silica gel, eluting with DCM and then with the DCM/MeOH (98/2; v/v) mixture. 2.39 g of the expected product are obtained in the form of an oil which crystallizes.

Workup

  1. waitthe mixture is left
  2. temperatureThe reaction mixture is cooled on an ice bath
  3. waitthe mixture is left
  4. stirringstirring overnight at RT
  5. extractionextracted with ether
  6. washthe organic phase washed with a saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated off under vacuum
  10. customThe residue is chromatographed on H silica gel
  11. washeluting with DCM

Sources & evidence

ORD record
ord-6942c51569884868a73a322912da4fbf
Source dataset
uspto-grants-2003_01
Patent number
US06506750B1

Reaction notes

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