Potassium Iodide → Ethyl 2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate

HRID 1613444Notes

Reaction equation

HRID 1613444 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[F:9][C:10]1[CH:11]=[C:12]([CH:21]=[C:22]([F:24])[CH:23]=1)[O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.Cl[CH2:26][CH2:27][NH:28][C:29](=[O:33])[O:30][CH2:31][CH3:32]>CN(C)C=O>[F:9][C:10]1[CH:11]=[C:12]([CH:21]=[C:22]([F:24])[CH:23]=1)[O:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:26][CH2:27][NH:28][C:29](=[O:33])[O:30][CH2:31][CH3:32])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 80621Ethyl 2-chloroethylcarbamateHCID 133918364-(3,5-Difluorophenoxy)phenol

Product 1

HCID 13502190Ethyl 2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamateYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

27.6 g of finely pulverulent potassium carbonate and 1.0 g of pulverized potassium iodide are added to a solution of 22.2 g of 4-(3,5-difluorophenoxy)phenol in 80 ml of dimethylformamide. 18.2 g of ethyl 2-chloroethylcarbamate are furthermore added dropwise, and the reaction mixture is heated for 16 hours at +95° C., with stirring. The reaction mixture is then filtered, the filtrate is poured into 400 ml of water, and the mixture is extracted three times using diethyl ether. The combined organic phases are washed with water and dried over sodium sulfate, and the solvent is distilled off. The residue is purified over silica gel (eluent: n-hexane/diethyl ether, 3:1), which gives pure ethyl 2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate as a colourless solid of melting point 54°-56° C., which solidifies in crystalline form; yield: 92% of theory.

Workup

  1. temperaturethe reaction mixture is heated for 16 hours at +95° C.
  2. filtrationThe reaction mixture is then filtered
  3. additionthe filtrate is poured into 400 ml of water
  4. extractionthe mixture is extracted three times
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationthe solvent is distilled off
  8. customThe residue is purified over silica gel (eluent: n-hexane/diethyl ether, 3:1), which

Sources & evidence

ORD record
ord-d639043afa244351a991bb54cb23bece
Source dataset
uspto-grants-1993_03
Patent number
US05192803

Reaction notes

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