Thioglycolic Acid → Diclazuril

HRID 355362Notes

Reaction equation

HRID 355362 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:19]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[C:21](C(O)=O)=[N:20]2)[CH:5]=[C:6]([Cl:18])[C:7]=1[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:9]#[N:10].SCC(O)=O.C(=O)([O-])O.[Na+]>O>[Cl:18][C:6]1[CH:5]=[C:4]([N:19]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[CH:21]=[N:20]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:9]#[N:10]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 516892Sodium BicarbonateHCID 189421702-(3,5-Dichloro-4-((RS)-(4-chlorophenyl)cyanomethyl)phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid2×

Product 1

HCID 456389Diclazuril

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 11.1 parts of 2-[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid (intermediate 5) and 15 parts of 2-mercaptoacetic acid is stirred and heated for 2 hours at 180 degrees C. The reaction mixture is cooled, water is added and the whole is treated with sodium hydrogen carbonate. The product is extracted with trichloromethane. The organic layer is dried, filtered and evaporated. The 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 in vacuo. The residue is stirred in 2,2'-oxybispropane. The product is filtered off and dried, yielding 2,6-dichloro-α-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetonitrile.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionThe product is extracted with trichloromethane
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated in vacuo
  10. stirringThe residue is stirred in 2,2'-oxybispropane
  11. filtrationThe product is filtered off
  12. customdried

Sources & evidence

ORD record
ord-5f21db4a99db4055ae42fdfb71a73b13
Source dataset
uspto-grants-1998_11
Patent number
US05830893

Reaction notes

Loading…