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2,6-dichloro-alpha-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-benzeneacetic acid → 2,6-dichloro-alpha-(4-chlorophenyl)-4-(3,4,5,6-tetrahydro-3,5-dioxo-1,2,4-triazin-2(1H)-yl)benzeneacetic acid

HRID 35565
Notes
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Reaction equation

HRID 35565 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]2)[CH:5]=[C:4]([Cl:16])[C:3]=1[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:18]([OH:20])=[O:19]>[Zn].C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH2:10][NH:9]2)[CH:5]=[C:4]([Cl:16])[C:3]=1[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:18]([OH:20])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 230351982,6-dichloro-alpha-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-benzeneacetic acid

Product 1

HCID 230351942,6-dichloro-alpha-(4-chlorophenyl)-4-(3,4,5,6-tetrahydro-3,5-dioxo-1,2,4-triazin-2(1H)-yl)benzeneacetic acidYield 67.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred and refluxed solution of 1.5 parts of 2,6-dichloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin2(3H)-yl)benzeneacetic acid in 100 parts of acetic acid were added 3 parts of zinc. Stirring was continued for 30 minutes at reflux temperature. The zinc salts were filtered off and the filtrate was evaporated. The residue was washed with water whereupon the solid product was filtered off and dissolved in a mixture of trichlorometmhane and methanol (90:10 by volume). The solution was dried, filtered and evaporated. The residue was washed with ethyl acetate and 2,2'-oxybispropane and dried, yielding 0.98 parts (67.2%) of 2,6-dichloro-α-(4-chlorophenyl)-4-(3,4,5,6-tetrahydro-3,5-dioxo-1,2,4-triazin-2(1H)-yl)benzeneacetic acid; mp. 194.2° C. (compound 1).

Workup

  1. stirringStirring
  2. temperatureat reflux temperature
  3. filtrationThe zinc salts were filtered off
  4. customthe filtrate was evaporated
  5. washThe residue was washed with water whereupon the solid product
  6. filtrationwas filtered off
  7. dissolutiondissolved in a mixture of trichlorometmhane and methanol (90:10 by volume)
  8. customThe solution was dried
  9. filtrationfiltered
  10. customevaporated
  11. washThe residue was washed with ethyl acetate and 2,2'-oxybispropane
  12. customdried

Sources & evidence

ORD record
ord-03fc46a2993547caacd55a12e1330a28
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04767760

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes