Hydrochloric Acid → Ethanone, 1-(2-bromo-4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-

HRID 648493Notes

Reaction equation

HRID 648493 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)OCC[O:10]1.Cl.[OH-].[Na+]>>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:10])[CH2:14][N:15]1[CH:19]=[N:18][CH:17]=[N:16]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20025739HCID 20025739, compound

Product 1

HCID 20025763Ethanone, 1-(2-bromo-4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-

Procedure

A mixture of 456 parts of 1-[[2-(2-bromo-4-chlorophenyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole and 1584 parts of concentrate hydrochloric acid was stirred and refluxed for 4 hours. The whole was treated with a sodium hydroxide solution 50%. After stirring for a while, the precipitated product I was filtered off, washed with water and set aside. The filtrate was extracted first twice with 4-methyl-2-pentanone and then three times with trichloromethane. The 4-methyl-2-pentanone layers were dried, filtered and evaporated. The residue was stirred in 2-propanol. The precipitated product II was filtered off and set aside. The trichloromethane-layers were dried, filtered and evaporated. The residue was stirred in 2-propanol. The precipitated product was filtered off and purified, together with product I and product II which were set aside, by column chromatography over silica gel using a mixture of dichloromethane, ethanol and ammonium hydroxide (98.5:1:0.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2' -oxybispropane and 2-propanol. The product was filtered off and dried, yielding 17 parts of 1-(2-bromo-4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (62).

Workup

  1. temperaturerefluxed for 4 hours
  2. stirringAfter stirring for a while
  3. filtrationthe precipitated product I was filtered off
  4. washwashed with water
  5. extractionThe filtrate was extracted first twice with 4-methyl-2-pentanone
  6. dry with materialThe 4-methyl-2-pentanone layers were dried
  7. filtrationfiltered
  8. customevaporated
  9. stirringThe residue was stirred in 2-propanol
  10. filtrationThe precipitated product II was filtered off
  11. dry with materialThe trichloromethane-layers were dried
  12. filtrationfiltered
  13. customevaporated
  14. stirringThe residue was stirred in 2-propanol
  15. filtrationThe precipitated product was filtered off
  16. custompurified, together with product I and product II which
  17. additiona mixture of dichloromethane, ethanol and ammonium hydroxide (98.5:1:0.5 by volume) as eluent
  18. customThe pure fractions were collected
  19. customthe eluent was evaporated
  20. customThe residue was crystallized from 2,2' -oxybispropane and 2-propanol
  21. filtrationThe product was filtered off
  22. customdried

Sources & evidence

ORD record
ord-c2da0ae24e4643a99e0d9c477facbe5a
Source dataset
uspto-grants-1988_04
Patent number
US04735942

Reaction notes

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