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

HRID 1613449Notes

Reaction equation

HRID 1613449 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([F:16])[CH:15]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(N(C(C)C)C(C)C)C.[C:26]1([S:32][N:33]([CH2:39][CH2:40]OS(C)(=O)=O)[C:34](=[O:38])[O:35][CH2:36][CH3:37])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(C=CC(O)=CC=1)O>CS(C)=O.N1C=CC=CC=1>[C:26]1([S:32][N:33]([CH2:39][CH2:40][O:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][C:4]3[CH:3]=[C:2]([F:1])[CH:15]=[C:14]([F:16])[CH:13]=3)=[CH:11][CH:10]=2)[C:34](=[O:38])[O:35][CH2:36][CH3:37])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 81531DiisopropylethylamineHCID 133918364-(3,5-Difluorophenoxy)phenolHCID 19775878ethyl N-phenylthio-2-methylsulfonyloxyethylcarbamate

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 1049PyridineSolvent

Procedure

A solution of 4.3 g of 4-(3,5-difluorophenoxy)phenol and 1.58 g of pyridine or 2.58 g of ethyl diisopropylamine in 35 ml of dry dimethyl sulfoxide is metered at a constant rate at +25° C. in the course of 5 hours to a solution of 6.4 g of ethyl N-phenylthio-2-methylsulfonyloxyethylcarbamate and 0.2 g of hydroquinone in 20 ml of anhydrous 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 three times 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 three times 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-b325ac67ca924cc9ad7f07f6653b5ff8
Source dataset
uspto-grants-1993_03
Patent number
US05192803

Reaction notes

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