Potassium Iodide → HCID 15042166, compound

HRID 2371689Notes

Reaction equation

HRID 2371689 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]2[O:7][C:8]([CH3:23])([CH3:22])[C@@H:9](OS(C)(=O)=O)[C@H:10]([NH:11][C:12](=[N:14][C:15]#[N:16])[CH3:13])[C:5]=2[CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>C(#N)C>[C:1]([C:3]1[CH:25]=[CH:24][C:6]2[O:7][C:8]([CH3:23])([CH3:22])[CH:9]=[C:10]([N:11]([C:12](=[N:14][C:15]#[N:16])[CH3:13])[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178464620HCID 178464620, compound

Product 1

HCID 15042166HCID 15042166, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.0 g of 6-cyano-2,2-dimethyl-4-[(N-cyano-acetimidoyl)amino]-2H-benzo[b]pyran obtained in Example 34 was suspended in 200 ml of acetonitrile, and 6.12 g of potassium carbonate, 0.75 g of potassium iodide and 7.53 g of ethyl bromoacetate were added thereto. The mixture was stirred under reflux for 2 hours. Then, the reaction mixture was cooled and then filtered to remove insoluble potassium carbonate and potassium bromide The filtrate was distilled to remove acetonitrile under reduced pressure. The residue was dissolved in 250 ml of ethyl acetate, washed with a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residual solid was recrystallized from ethyl acetate/n-hexane to obtain 4.8 g of the above identified compound in the form of crystals.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThen, the reaction mixture was cooled
  3. filtrationfiltered
  4. customto remove insoluble potassium carbonate and potassium bromide The filtrate
  5. distillationwas distilled
  6. customto remove acetonitrile under reduced pressure
  7. dissolutionThe residue was dissolved in 250 ml of ethyl acetate
  8. washwashed with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThen, ethyl acetate was distilled off under reduced pressure
  11. customThe residual solid was recrystallized from ethyl acetate/n-hexane
  12. customto obtain 4.8 g of the

Sources & evidence

ORD record
ord-1436322a734b4d8d89cc9b67e72eee67
Source dataset
uspto-grants-1992_03
Patent number
US05095016

Reaction notes

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