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Thioglycolic Acid → Diclazuril

HRID 355362
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 355362
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 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×

Produkt 1

HCID 456389Diclazuril

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5f21db4a99db4055ae42fdfb71a73b13
Quelldatensatz
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05830893

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