Hydroquinone → ethyl N-phenylthio-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate

HRID 1613448Notes

Reaction equation

HRID 1613448 reaction equation
[Na].[F:2][C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([F:17])[CH:16]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[H-].[Na+].[C:20]1([S:26][N:27]([CH2:33][CH2:34]OS(C)(=O)=O)[C:28](=[O:32])[O:29][CH2:30][CH3:31])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(C=CC(O)=CC=1)O>CS(C)=O>[C:20]1([S:26][N:27]([CH2:33][CH2:34][O:13][C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:4]=[C:3]([F:2])[CH:16]=[C:15]([F:17])[CH:14]=3)=[CH:12][CH:11]=2)[C:28](=[O:32])[O:29][CH2:30][CH3:31])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 785HydroquinoneHCID 24758Sodium hydrideHCID 5360545SodiumHCID 133918364-(3,5-Difluorophenoxy)phenol2×HCID 19775878ethyl N-phenylthio-2-methylsulfonyloxyethylcarbamate

Product 1

HCID 19775874ethyl N-phenylthio-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of the sodium salt of 4-(3,5-difluorophenoxy)phenol (prepared from 4.3 g of 4-(3,5-difluorophenoxy)phenol and 0.8 g of a 55% dispersion of sodium hydride in mineral oil in 40 ml of dry dimethyl sulfoxide) is metered at a constant rate at +25° C. in the course of 5 hours to a solution of 6.5 g of ethyl N-phenylthio-2-methylsulfonyloxyethylcarbamate and 0.1 g of hydroquinone in 20 ml of anhydrons dimethyl sulfoxide, with stirring. The mixture is stirred for 5 more hours at room temperature. After this, the reaction mixture is poured into ice-water and extracted repeatedly with an ether/hexane mixture (1:4), and the combined organic phases are washed with water and dried over sodium sulfate. After the solvents have been distilled off in vacuo, the crude product is purified by chromatography, by which process ethyl N-phenylthio-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate is isolated, nD20 : 1.5700.

Workup

  1. stirringThe mixture is stirred for 5 more hours at room temperature
  2. extractionextracted repeatedly with an ether/hexane mixture (1:4)
  3. washthe combined organic phases are washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationAfter the solvents have been distilled off in vacuo
  6. customthe crude product is purified by chromatography, by which process ethyl N-phenylthio-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate
  7. customis isolated

Sources & evidence

ORD record
ord-eacd68f7009842229a57769c4099686d
Source dataset
uspto-grants-1993_03
Patent number
US05192803

Reaction notes

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