Dichloromethane → 2-(2-Hydroxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

HRID 544653Notes

Reaction equation

HRID 544653 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10](C3C=CC(OC)=CC=3)[C:11](=[S:14])[S:12][CH:13]=2)=[CH:5][CH:4]=1.Br[CH2:24][CH2:25][OH:26].C(Cl)Cl>[OH-].[Na+]>[OH:26][CH2:25][CH2:24][S:14][C:11]1[S:12][C:13]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 108982-BromoethanolHCID 129255794,3-Bis-(p-methoxyphenyl)-thiazoline-2-thione

Product 1

HCID 132096672-(2-Hydroxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

100 g of 4,3-bis-(p-methoxyphenyl)-thiazoline-2-thione are dissolved in 320 ml of 2 N sodium hydroxide solution while stirring. 45 ml of 2-bromoethanol are then added, the mixture is stirred at room temperature for 15 minutes, 500 ml of methylene chloride are added, the mixture is filtered through diatomaceous earth, the organic layer is removed and extracted by washing with 200 ml of 2 N sodium hydroxide solution. The combined aqueous phases are subsequently extracted twice with methylene chloride. The organic phases are combined, dried over magnesium sulphate and concentrated by evaporation under reduced pressure. The remaining oil is dissolved in 700 ml of hot diethyl ether, stirred for 1 hour and caused to crystallise at 10°. The crystals are filtered with suction, then washed twice with 150 ml of ice-cold diethyl ether each time and dried under reduced pressure. 2-(2-Hydroxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole having a melting point of 82°-83° is obtained.

Workup

  1. stirringthe mixture is stirred at room temperature for 15 minutes
  2. filtrationthe mixture is filtered through diatomaceous earth
  3. customthe organic layer is removed
  4. extractionextracted
  5. washby washing with 200 ml of 2 N sodium hydroxide solution
  6. extractionThe combined aqueous phases are subsequently extracted twice with methylene chloride
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. dissolutionThe remaining oil is dissolved in 700 ml of hot diethyl ether
  10. stirringstirred for 1 hour
  11. customto crystallise at 10°
  12. filtrationThe crystals are filtered with suction
  13. washwashed twice with 150 ml of ice-cold diethyl ether each time
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-3909e5582205424a87b7d71e9b2b38f1
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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