Potassium Carbonate → HCID 15172317, compound

HRID 1195601Notes

Reaction equation

HRID 1195601 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[O:4][NH:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH2:23]([O:25][CH2:26]Cl)[CH3:24]>O>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[O:4][N:5]([CH2:26][O:25][CH2:23][CH3:24])[C:6](=[O:11])[NH:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18523Chloromethyl ethyl etherHCID 13746391HCID 13746391, compound

Product 1

HCID 15172317HCID 15172317, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 2.63 g of 3-(2,5-dichlorophenoxy)-1-n-propylurea, were added 4.14 g (20 mmoles) of anhydrous potassium carbonate and then 1.42 g (15 mmoles) of chloromethyl ethyl ether. The mixture was stirred at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, and 300 ml of water was added. The mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The ethyl acetate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane) to give 0.44 g (yield 14 %) of the desired compound as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe ethyl acetate was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-38091998b58e4627b404b8593c683403
Source dataset
uspto-grants-1992_05
Patent number
US05112385

Reaction notes

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