1H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]- → 1-[2-(2,4-Dichlorophenyl)-2-hydroxy-3-(1-methylimidazol-2-ylthio)-propyl]-1,2,4-triazole

HRID 2118491Notes

Reaction equation

HRID 2118491 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.[SH:18][C:19]1[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([CH2:11][S:18][C:19]1[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=1)[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1

Participants

4

Reactant 2

HCID 104232291H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]-HCID 178480602HCID 178480602, compound

Product 1

HCID 201939451-[2-(2,4-Dichlorophenyl)-2-hydroxy-3-(1-methylimidazol-2-ylthio)-propyl]-1,2,4-triazoleYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl-methyl)-oxirane (0.27 g, 0.001 m), and 2-mercapto-1-methylimidazole (0.228 g, 0.002 m) were heated under reflux in dioxan for 72 hours. The dioxan was then evaporated and the residue was dissolved in ethyl acetate (70 ml). This solution was washed sequentially with dilute potassium carbonate solution, dilute sodium hydroxide solution, and water dried (MgSO4) and evaporated to give an oil which crystallized on standing. Recrystallization from ethyl acetate/hexane gave the title compound 0.252 g (66%); m.p. 159°-161° C.

Workup

  1. customThe dioxan was then evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (70 ml)
  3. washThis solution was washed sequentially with dilute potassium carbonate solution, dilute sodium hydroxide solution, and water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give an oil which
  7. customcrystallized
  8. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-90d982b6a7664c1e9b9f06b2340b6c9a
Source dataset
uspto-grants-1987_07
Patent number
US04678789

Reaction notes

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