Sodium Iodide → HCID 22707973, compound

HRID 353214Notes

Reaction equation

HRID 353214 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:11][C:10](=[O:12])[C:9]([C:13]#[N:14])=[CH:8][CH:7]=1.Cl[CH2:16][C:17]([NH2:19])=[O:18].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C.O>[C:13]([C:9]1[C:10]([O:12][CH2:16][C:17]([NH2:19])=[O:18])=[N:11][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][CH:8]=1)#[N:14]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 27470886-(Furan-2-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 22707973HCID 22707973, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 6-(2-furyl)-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (6.0 g, 32.3 mmol), 2-chloroacetamide (3.0 g, 37.7 mmol), sodium iodide (5.7 g, 38.0 mmol) and potassium carbonate (9.0 g, 56.2 mmol) in acetone (100 ml) was stirred at 60° C. for 6 hours. After cooling as it was, the reaction solution was diluted with ethyl acetate and water. The organic layer was washed with an aqueous saturated solution of sodium bicarbonate (×2) and an aqueous saturated solution of ammonium chloride, dried over anhydrous sodium sulfate, and concentrated. Diethyl ether was added to the residue, and the resulting precipitates were collected by filtration and washed with diethyl ether, to give the title compound (4.2 g, 54%) as a brown solid.

Workup

  1. temperatureAfter cooling as it
  2. washThe organic layer was washed with an aqueous saturated solution of sodium bicarbonate (×2)
  3. dry with materialan aqueous saturated solution of ammonium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionDiethyl ether was added to the residue
  6. customthe resulting precipitates
  7. filtrationwere collected by filtration
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-569a59fcda26478c847ca0dbbecc57a7
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

Loading…