Hydrochloric Acid → 1-[2-(2,4-dichlorophenyl)-2-hydroxy-3-mercaptopropyl]-1H-1,2,4-triazole

HRID 2164608Notes

Reaction equation

HRID 2164608 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH2:11][O:10]1.C(=O)(O)[O-].[Na+].[O-]CC.[Na+].Cl.[S:28]1C=CC=C1CC(O)=O>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([CH2:11][SH:28])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 159702-Thiopheneacetic acidHCID 516892Sodium Bicarbonate2×HCID 2723922Sodium ethoxideHCID 104232291H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]-

Product 1

HCID 202058911-[2-(2,4-dichlorophenyl)-2-hydroxy-3-mercaptopropyl]-1H-1,2,4-triazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl-methyl)-oxirane, 5 g, (0.0185 mole) was heated under mild reflux in thiolacetic acid (CH3COSH) (5 ml) for three hours. The mixture was then cooled and added to a mixture of ice-cooled saturated sodium bicarbonate solution (200 ml) and ethyl acetate (200 ml) and the aqueous layer was separated. The organic layer was washed a further four times with ice-cooled saturated sodium bicarbonate solution (200 ml in total), dried over magnesium sulphate and evaporated to give a red gum which was dissolved in ethanol (20 ml). This solution was added dropwise over 15 minutes to a stirred and ice-cooled solution of sodium ethoxide (3.78 g, 0.0556 mole) in ethanol (100 ml). After one hour the mixture was poured into 1N hydrochloric acid (100 ml) and this solution was then neutralized by addition of solid sodium bicarbonate. Extraction with dichloromethane (6×50 ml), drying over magnesium sulphate, and evaporation of the combined extracts gave a gum which was chromatographed on silica, eluting with ethyl acetate, to give after one recrystallization from ethyl acetate/hexane the title compound, yield 2.3 g, m.p., 139°-142.5° C.

Workup

  1. temperatureThe mixture was then cooled
  2. additionadded to a mixture of ice-
  3. customthe aqueous layer was separated
  4. washThe organic layer was washed a further four times with ice-
  5. temperaturecooled saturated sodium bicarbonate solution (200 ml in total)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customto give a red gum which
  9. additionThis solution was added dropwise over 15 minutes to
  10. extractionExtraction with dichloromethane (6×50 ml)
  11. dry with materialdrying over magnesium sulphate, and evaporation of the combined extracts
  12. customgave a gum which
  13. customwas chromatographed on silica
  14. washeluting with ethyl acetate
  15. customto give
  16. customafter one recrystallization from ethyl acetate/hexane the title compound, yield 2.3 g, m.p., 139°-142.5° C.

Sources & evidence

ORD record
ord-74e6294bbe7841a7ba7c2c659e45034e
Source dataset
uspto-grants-1985_03
Patent number
US04505919

Reaction notes

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