Potassium Hydroxide → HCID 19348157, compound

HRID 1637278Notes

Reaction equation

HRID 1637278 reaction equation
[C:1]([N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[CH:13](Br)[CH2:14][CH2:15][CH:6]([C:7]=23)[CH:5]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:3])[CH3:2].[OH-].[K+]>CN1CCN(C)C1=O.O>[C:1]([N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[CH:13]=[CH:14][CH2:15][CH:6]([C:7]=23)[CH:5]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19348335HCID 19348335, compound

Product 1

HCID 19348157HCID 19348157, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
110 °C

Procedure

A portion (5.60 g) of the compound obtained in Example 161 was dissolved in dimethylimidazolidone (DMI; 100 ml) and to the solution was added potassium hydroxide powder (1.46 g). The mixture was heated for 1 hour at 110° C. and allowed to cool. The reaction mixture was diluted with water and extracted three times with ethyl acetate. The organic layers were combined, washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure and the residue was crystallized from ether to yield 3.70 g (86%) of the titled compound as white crystals.

Workup

  1. temperatureto cool
  2. extractionextracted three times with ethyl acetate
  3. washwashed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-d0ffa553a16d48fc8b402850d1cef5e1
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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