2-Mercaptoethanol → HCID 15029144, compound

HRID 2248238Notes

Reaction equation

HRID 2248238 reaction equation
[Br: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>[Br: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

6

Reactant 3

HCID 15672-MercaptoethanolHCID 6101p-Toluenesulfonic acidHCID 6031611-(4-Bromophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

Product 1

HCID 15029144HCID 15029144, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 1140TolueneSolvent

Procedure

To a slurry of 27.8 g 1-(4-bromophenyl)-2-(1H-1,2,4-triazol-1-yl) ethanone in 350 ml dry toluene and 175 ml 1-butanol were added 15.6 g 2-mercaptoethanol and 24.7 g p-toluenesulfonic acid. The mixture was refluxed under a Dean-Stark trap for 50 hours. After cooling, a white solid was removed by filtration and the filtrate evaporated. The residue was taken up in chloroform and washed twice with 10% aqueous sodium hydroxide and once with water. The organic layer was dried, filtered and evaporated to leave a liquid residue. The 1-butanol in the residue was removed azeotropically three times with cyclohexane leaving a slurry. The solid was isolated by filtration to give 5.2 g of product.

Workup

  1. temperatureThe mixture was refluxed under a Dean-Stark trap for 50 hours
  2. temperatureAfter cooling
  3. customa white solid was removed by filtration
  4. customthe filtrate evaporated
  5. washwashed twice with 10% aqueous sodium hydroxide and once with water
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated
  9. customto leave a liquid residue
  10. customThe 1-butanol in the residue was removed azeotropically three times with cyclohexane leaving a slurry
  11. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-a732bb7a4d3647e2b87e418ae0485797
Source dataset
uspto-grants-1991_08
Patent number
US05039332

Reaction notes

Loading…