2-Mercaptoethanol → HCID 19430498, compound

HRID 1077878Notes

Reaction equation

HRID 1077878 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.[SH:16][CH2:17][CH2:18]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(O)CCC.C1CCCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:9][N:10]3[CH:14]=[N:13][CH:12]=[N:11]3)[S:16][CH2:17][CH2:18][O:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 15672-MercaptoethanolHCID 6101p-Toluenesulfonic acidHCID 7164721-(4-Chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

Product 1

HCID 19430498HCID 19430498, compoundYield 27.9%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 1140TolueneSolventHCID 8078CyclohexaneSolvent

Procedure

To a slurry of 44.3 g 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl) ethanone in 800 ml dry toluene and 400 ml 1-butanol was added 31.2 g 2-mercaptoethanol and 51.0 g p-toluenesulfonic acid. The mixture was refluxed under a Dean-Stark trap for 48 hours. On cooling, a white solid precipitated out, which was removed by filtration. The filtrate was evaporated, the residue dissolved in dichloromethane and washed twice with 10% aqueous sodium hydroxide and once with water. The organic layer was dried, filtered and evaporated to leave an oil which was taken up in cyclohexane. The cyclohexane was evaporated to azeotrope off any remaining 1-butanol, leaving an oily solid which was triturated with petroleum ether to give 15.7 g of product.

Workup

  1. temperatureThe mixture was refluxed under a Dean-Stark trap for 48 hours
  2. temperatureOn cooling
  3. customa white solid precipitated out
  4. customwhich was removed by filtration
  5. customThe filtrate was evaporated
  6. dissolutionthe residue dissolved in dichloromethane
  7. washwashed twice with 10% aqueous sodium hydroxide and once with water
  8. customThe organic layer was dried
  9. filtrationfiltered
  10. customevaporated
  11. customto leave an oil which
  12. customThe cyclohexane was evaporated
  13. customleaving an oily solid which
  14. customwas triturated with petroleum ether

Sources & evidence

ORD record
ord-e193fd2e07704a1b86bee3abd88407c6
Source dataset
uspto-grants-1996_08
Patent number
US05545655

Reaction notes

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