m-Chloroperbenzoic acid → 2-(2-Hydroxyethanesulphinyl)-4,5-bis-(p-methoxyphenyl)-thiazole

HRID 544658Notes

Reaction equation

HRID 544658 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[S:6][C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:9]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)Cl>[OH:1][CH2:2][CH2:3][S:4]([C:5]1[S:6][C:7]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[N:9]=1)=[O:34]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 132096672-(2-Hydroxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

Product 1

HCID 204583532-(2-Hydroxyethanesulphinyl)-4,5-bis-(p-methoxyphenyl)-thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g of 2-(2-hydroxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole are dissolved in 100 ml of methylene chloride and, while stirring, 2.56 g of m-chloroperbenzoic acid are added in portions. The mixture is then stirred for 15 minutes and subsequently extracted by shaking twice with dilute sodium carbonate solution. The aqueous phase is then washed with methylene chloride. The organic phases are combined, dried over magnesium sulphate and concentrated to dryness by evaporation. The crude product is dissolved in 10 ml of ethyl acetate, precipitated with 30 ml of diethyl ether, filtered with suction, washed with diethyl ether, dried under reduced pressure and, to purify further, made into a slurry with 50 ml of diethyl ether, filtered again and dried at 0.01 mbar and 100° to constant weight. 2-(2-hydroxyethanesulphinyl)-4,5-bis-(p-methoxyphenyl)-thiazole is obtained in the form of a pale yellow oil, Rf value 0.12 (silica gel thin layer/toluene:ethyl acetate 1:1); IR-spectrum: νSO =1060 cm-1 (3% in CH2Cl2).

Workup

  1. stirringThe mixture is then stirred for 15 minutes
  2. extractionsubsequently extracted
  3. stirringby shaking twice with dilute sodium carbonate solution
  4. washThe aqueous phase is then washed with methylene chloride
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness by evaporation
  7. dissolutionThe crude product is dissolved in 10 ml of ethyl acetate
  8. customprecipitated with 30 ml of diethyl ether
  9. filtrationfiltered with suction
  10. washwashed with diethyl ether
  11. customdried under reduced pressure
  12. customto purify further
  13. filtrationfiltered again
  14. customdried at 0.01 mbar and 100° to constant weight

Sources & evidence

ORD record
ord-dbb437ff34a04a60b8967cb1f62feca1
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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