Potassium Iodide → HCID 23334095, compound

HRID 904305Notes

Reaction equation

HRID 904305 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[OH:12])[O:5][C:4](=[O:13])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+].[I-].[K+].[O:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34]Cl)[CH2:29][CH2:28]1>C(Cl)(Cl)Cl.C(C(C)=O)C(C)C>[O:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][O:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[OH:12])[O:5][C:4](=[O:13])[C:3]=2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 767274-(2-Chloroethyl)morpholineHCID 516892Sodium BicarbonateHCID 54702662HCID 54702662, compound

Product 1

HCID 23334095HCID 23334095, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

76.3 g. (0.3 mol) of 4,5-dihydroxy-3-phenyl-coumarin (Example 23a), 25.2 g. (0.3 mol) of sodium bicarbonate, 3 g. of potassium iodide and 800 ml. of methyl isobutyl ketone are brought over one hour to 80° C. The mixture is then cooled to 60° C., whereafter 48.4 g. (0.324 mol) of 2-morpholino-1-chlorethane are added dropwise and the temperature is brought over 8 hours to 100° C. It is then left at room temperature for one night and filtered. The precipitate obtained is taken up in 1 liter of chloroform. The light, insoluble substance obtained is filtered and the chloroform is evaporated under vacuum. The residue obtained is recrystallised from 700 ml. of methyl isobutyl ketone. 50 g. of a white product are isolated. M.P. 206° C.; yield 44.5% (theoretical yield 110.2 g.).

Workup

  1. waitIt is then left at room temperature for one night
  2. filtrationfiltered
  3. customThe precipitate obtained
  4. customThe light, insoluble substance obtained
  5. filtrationis filtered
  6. customthe chloroform is evaporated under vacuum
  7. customThe residue obtained
  8. customis recrystallised from 700 ml
  9. customof a white product are isolated

Sources & evidence

ORD record
ord-f69565ab3ccd4ea79b685c590f457d67
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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