Potassium Iodide → 4-(2'-Diethylaminoethoxy)-3-phenyl-coumarin

HRID 904288Notes

Reaction equation

HRID 904288 reaction equation
[C:1]1([C:7]2[C:8](=[O:18])[O:9][C:10]3[C:15]([C:16]=2[OH:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31]Cl)[CH3:28]>C(C(C)=O)C(C)C>[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31][O:17][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:9][C:8](=[O:18])[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:28]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chlorideHCID 54688870Coumarin, 4-hydroxy-3-phenyl-

Product 1

HCID 233340754-(2'-Diethylaminoethoxy)-3-phenyl-coumarin

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent2×

Procedure

11.9 g. (0.05 mol) of 3-phenyl-4-hydroxy-coumarin, 8.3 g. (0.06 mol) of anhydrous potassium carbonate and 200 ml. of methyl isobutyl ketone are placed in a dry reactor. The mixture is brought while stirring for 1 hour to 70° C. 0.5 g. of potassium iodide is then added, followed by dropwise addition of a solution of 8.8 g. (0.065 mol) of 2-diethylamino-1-chlorethane in 20 ml. of methyl isobutyl ketone.

Workup

  1. additionfollowed by dropwise addition of a solution of 8.8 g

Sources & evidence

ORD record
ord-eeb5a0d4325c41dca7762411f9ff93b5
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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