Potassium Iodide → HCID 23334032, compound

HRID 904306Notes

Reaction equation

HRID 904306 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[OH:20])[O:13][C:12](=[O:21])[C:11]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:3][CH2:2]1.[C:28](=O)([O-])[O-].[K+].[K+].[I-].[K+].S(OC)(OC)(=O)=O>C(C(C)=O)C(C)C>[CH3:28][O:20][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[C:10]([O:9][CH2:8][CH2:7][N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)=[C:11]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:12](=[O:21])[O:13]2

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 23334095HCID 23334095, compound

Product 1

HCID 23334032HCID 23334032, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

18.4 g. (0.05 mol) of 4-(2'-morpholinoethoxy)-5-hydroxy-3-phenyl coumarin (Example 30), 9.7 g. (0.07 mol) of potassium carbonate, 0.5 g. of potassium iodide and 250 ml. of methyl isobutyl ketone are brought over one hour to 80° C. The temperature is then brought to 60° C. and 7.6 g. (0.06 mol) of freshly distilled dimethyl sulphate are added dropwise in 20 minutes. Refluxing takes place for 8 hours and, after cooling, filtering is carried out. The filtrate is evaporated under vacuum and then, after washing with sodium bicarbonate and then water, and extraction with chloroform, there are obtained, after evaporation, 4.8 g. of an oil which cannot be crystallised. Yield 25.2% (theoretical yield 19.1 g.).

Workup

  1. customis then brought to 60° C.
  2. temperatureRefluxing
  3. customfor 8 hours
  4. temperatureafter cooling
  5. filtrationfiltering
  6. customThe filtrate is evaporated under vacuum
  7. washafter washing with sodium bicarbonate
  8. extractionwater, and extraction with chloroform, there
  9. customare obtained
  10. customafter evaporation, 4.8 g
  11. customof an oil which cannot be crystallised

Sources & evidence

ORD record
ord-9c9f19eb22404864ae51dcb032e3bd89
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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