Potassium Carbonate → Ethyl 2-(2-chloro-5-phenoxyphenoxy)ethylcarbamate

HRID 2226191Notes

Reaction equation

HRID 2226191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[OH:15].Cl[CH2:17][CH2:18][NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[O:15][CH2:17][CH2:18][NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80621Ethyl 2-chloroethylcarbamateHCID 7922452-Chloro-5-phenoxyphenol

Product 1

HCID 18966621Ethyl 2-(2-chloro-5-phenoxyphenoxy)ethylcarbamateYield 10.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.91 g of 2-chloro-5-phenoxyphenol in 20 ml of N,N-dimethylformamide, there were added 0.69 g of ethyl 2-chloroethylcarbamate and 1.14 g of potassium carbonate with stirring, and the resultant mixture was stirred at 50° C. for 7 hours. The reaction mixture was poured into 100 g of ice-water and extracted twice with 100 ml of ethyl acetate. The extracts were combined together, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 0.14 g of ethyl 2-(2-chloro-5-phenoxyphenoxy)ethylcarbamate. Yield: 10%. nD22 : 1.5608.

Workup

  1. extractionextracted twice with 100 ml of ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e2cfe73c1dc40d9aca8a69d35d1f2b2
Source dataset
uspto-grants-1994_09
Patent number
US05346920

Reaction notes

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