Potassium Iodide → HCID 19805550, compound

HRID 2248141Notes

Reaction equation

HRID 2248141 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>CC(=O)CC>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[O:20][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 54443074HCID 54443074, compound

Product 1

HCID 19805550HCID 19805550, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 12.79 g. (47.1 mMol) 3-[2-(benzyloxycarbonylamino)-ethyl]-phenol, 120 ml. butan-2-one and 19.5 g. pulverised potassium carbonate is maintained at reflux temperature for 1 hour, then cooled, 200 mg. pulverised potassium iodide and 9.12 g. (51.9 mMol) ethyl bromoacetate added thereto and the reaction mixture stirred for 18 hours at 90° C. Subsequently, it is filtered off with suction and the filter cake is washed with hot butan-2-one. The combined butanone phases are evaporated, the oily residue is taken up in diethyl ether and the ethereal phase is extracted twice with ice-cold 2N aqueous sodium hydroxide solution, and thereafter with ice water. After drying with anhydrous sodium sulphate, it is evaporated in a vacuum. There are obtained 15.62 g. (93% of theory) of the desired product in the form of a colourless oil.

Workup

  1. additionA suspension of 12.79 g
  2. temperatureis maintained
  3. temperatureat reflux temperature for 1 hour
  4. temperaturecooled
  5. filtrationSubsequently, it is filtered off with suction
  6. washthe filter cake is washed with hot butan-2-one
  7. customThe combined butanone phases are evaporated
  8. extractionthe ethereal phase is extracted twice with ice-cold 2N aqueous sodium hydroxide solution
  9. dry with materialAfter drying with anhydrous sodium sulphate, it
  10. customis evaporated in a vacuum
  11. customThere are obtained 15.62 g

Sources & evidence

ORD record
ord-16efe11f44ee4b569a6467695c43ce6c
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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