Oxalic Acid → 3-(4-methyl-1-piperazinylmethyl)-4-(3-o-chlorobenzoyl-5-ethyl-2-thienyl)-5-methyl-4H-1,2,4-triazole dioxalate

HRID 1606044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1606044
S(O[CH2:12][C:13]1[N:17]([C:18]2[S:19][C:20]([CH2:32][CH3:33])=[CH:21][C:22]=2[C:23](=[O:31])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:16]([CH3:34])=[N:15][N:14]=1)(C1C=CC(C)=CC=1)(=O)=O.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44]>C(O)C>[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44].[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44].[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([CH2:12][C:13]2[N:17]([C:18]3[S:19][C:20]([CH2:32][CH3:33])=[CH:21][C:22]=3[C:23](=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[C:16]([CH3:34])=[N:15][N:14]=2)[CH2:38][CH2:37]1

Komponenten

5

Edukt 3

HCID 971Oxalic AcidHCID 531671-MethylpiperazineHCID 545721073-tosyloxymethyl-4-(3-o-chlorobenzoyl-5-ethyl-2-thienyl)-5-methyl-4H-1,2,4-triazole

Produkt 1

HCID 867332583-(4-methyl-1-piperazinylmethyl)-4-(3-o-chlorobenzoyl-5-ethyl-2-thienyl)-5-methyl-4H-1,2,4-triazole dioxalateAusbeute 49,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a suspension of 7 g of 3-tosyloxymethyl-4-(3-o-chlorobenzoyl-5-ethyl-2-thienyl)-5-methyl-4H-1,2,4-triazole in 100 ml of ethanol is added 2 g of N-methyl-piperazine, and the mixture is refluxed for 5 hours. Aftr the completion of the reaction, the solvent is distilled off and water is added to the residue. The residue is made alkaline with potassium carbonate and extracted with ethyl acetate. The extract is washed with water and dried over anhydrous sodium sulfate. The solvent is distilled off and the residue obtained is allowed to react with 2.2 g of oxalic acid in ethanol. The crude crystals formed are recrystallized from aqueous ethanol to give 3.8 g of 3-(4-methyl-1-piperazinylmethyl)-4-(3-o-chlorobenzoyl-5-ethyl-2-thienyl)-5-methyl-4H-1,2,4-triazole dioxalate 1/2 hydrate as colorless crystals melting at 164° - 165°C (decomposition).

Aufarbeitung

  1. temperaturethe mixture is refluxed for 5 hours
  2. customAftr the completion of the reaction
  3. distillationthe solvent is distilled off
  4. additionwater is added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent is distilled off
  9. customthe residue obtained
  10. customThe crude crystals formed
  11. customare recrystallized from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-425f70e40fb2439894de0856179cb3ae
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03952006

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