Formaldehyde → 4-allyl-2-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-5-(3-pyridyl)-1,2,4-triazole-3(2H,4H)-thione

HRID 1952756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1952756
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.[CH2:17]([N:20]1[C:24]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[N:23][NH:22][C:21]1=[S:31])[CH:18]=[CH2:19].[CH2:32]=O>C(O)(C)(C)C>[CH2:17]([N:20]1[C:24]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[N:23][N:22]([CH2:32][N:14]2[CH2:15][CH2:16][N:11]([C:10]3[C:5]4[O:4][CH2:3][CH2:2][O:1][C:6]=4[CH:7]=[CH:8][CH:9]=3)[CH2:12][CH2:13]2)[C:21]1=[S:31])[CH:18]=[CH2:19]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 65853EltoprazineHCID 7582884-Allyl-5-pyridin-3-yl-4H-[1,2,4]triazole-3-thiol

Produkt 1

HCID 867557224-allyl-2-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-5-(3-pyridyl)-1,2,4-triazole-3(2H,4H)-thione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(1,4-benzodioxan-5-yl)piperazine (1 g; prepared in a similar manner to that described in Example 2), 4-allyl-5-(3-pyridyl)-1,2,4-triazole-3(2H,4H)-thione (1 g), 37-40% aqueous formaldehyde solution (0.5 ml) and t-butanol (60 ml) was stirred at ambient temperature for 30 minutes, heated under reflux for 15 minutes, then the solvent was removed in vacuo. The residue was triturated with a 1:1 mixture of cyclohexane and ether (40 ml), and the resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 4-allyl-2-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-5-(3-pyridyl)-1,2,4-triazole-3(2H,4H)-thione as a white solid (0.62 g), m.p. 122-127° C.

Aufarbeitung

  1. customprepared in a similar manner to that
  2. temperatureheated
  3. temperatureunder reflux for 15 minutes
  4. customthe solvent was removed in vacuo
  5. customThe residue was triturated with a 1:1 mixture of cyclohexane and ether (40 ml)
  6. filtrationthe resulting solid was collected by filtration
  7. customdried in vacuo at ambient temperature

Quellen und Nachweise

ORD-Eintrag
ord-70b63dc3274e4ac28a5f8d468fbf25e5
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06114334

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