Dimethyl Sulfoxide → 1-[2-(2,4-dichlorophenyl)-2-(2-propynyloxy)ethyl]-1H-1,2,4-triazole

HRID 745284Notes

Reaction equation

HRID 745284 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.CS(C)=O.[H-].[Na+].Cl[CH2:24][C:25]#[CH:26]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([O:16][CH2:26][C:25]#[CH:24])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 122213-Chloro-1-propyneHCID 24758Sodium hydrideHCID 66285758905-18-3

Product 1

HCID 136554291-[2-(2,4-dichlorophenyl)-2-(2-propynyloxy)ethyl]-1H-1,2,4-triazoleYield 33.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.2 parts of α-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-ethanol, 50 parts of dimethyl sulfoxide and 45 parts of benzene is stirred till all solid enters solution. Then there is added 1 part of a sodium hydride dispersion 78% and stirring is continued till gasevolution has ceased. After stirring for one hour at 40°-50° C., there are added 2.3 parts of 3-chloro-1-propyne. The whole is stirred overnight at room temperature. The reaction mixture is poured onto ice-water and the product is extracted with 1,1'-oxybisethane. The extract is washed with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. Upon standing overnight at room temperature, the residue solidifies. The product is filtered off and crystallized from 2,2'-oxybispropane, yielding 2 parts (33.8%) of 1-[2-(2,4-dichlorophenyl)-2-(2 -propynyloxy)ethyl]-1H-1,2,4-triazole; mp. 84° C.

Workup

  1. stirringstirring
  2. stirringAfter stirring for one hour at 40°-50° C.
  3. stirringThe whole is stirred overnight at room temperature
  4. additionThe reaction mixture is poured onto ice-water
  5. extractionthe product is extracted with 1,1'-oxybisethane
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated
  14. filtrationThe product is filtered off
  15. customcrystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-61ba752124374f02a74af18841714324
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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