Sodium hydride → HCID 13365280, compound

HRID 615318Notes

Reaction equation

HRID 615318 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[C:13](=[O:14])[NH:12][C:11]([S:15][CH3:16])=[C:10]2[C:17]#[N:18])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:28][N:29]([CH3:34])[CH2:30][CH2:31][CH2:32]Cl>O1CCOCC1>[CH3:25][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[C:13](=[O:14])[N:12]([CH2:32][CH2:31][CH2:30][N:29]([CH3:34])[CH3:28])[C:11]([S:15][CH3:16])=[C:10]2[C:17]#[N:18])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 132362024-[4-(Dimethylamino)phenyl]-2-(methylsulfanyl)-5-oxo-4-(pyridin-3-yl)-4,5-dihydro-1H-pyrrole-3-carbonitrile

Product 1

HCID 13365280HCID 13365280, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 3.5 g 4-(4-dimethylaminophenyl)-2-methylthio-5-oxo-4-(3-pyridyl)-2-pyrroline-3-carbonitrile and 0.3 g sodium hydride (80% in white oil) is refluxed for one hour. One then adds dropwise thereto, within ten minutes, a solution of 1.3 g 3-dimethylaminopropyl chloride in 25 ml abs. dioxan and further boils for six hours. After cooling, the reaction mixture is filtered, the solvent is removed on a Rotavapor and the residue is chromatographed on silica gel with chloroform+methanol 10+1 as elution agent. After crystallization of the main fraction from isopropanol, one obtains 1.8 g of colorless crystals of mp 90°-91° C.

Workup

  1. temperatureis refluxed for one hour
  2. additionOne then adds dropwise
  3. waitwithin ten minutes
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture is filtered
  6. customthe solvent is removed on a Rotavapor
  7. customthe residue is chromatographed on silica gel with chloroform+methanol 10+1 as elution agent
  8. customAfter crystallization of the main fraction from isopropanol, one

Sources & evidence

ORD record
ord-0b9af09f6446479f877c6223c5568365
Source dataset
uspto-grants-1985_02
Patent number
US04499089

Reaction notes

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