3-ethyl-1H-pyrazol-5-amine → 4-(2,4-Dichlorophenyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazine

HRID 1061545

Reaktionsgleichung

Reaktionsgleichung von HRID 1061545
[NH2:1][C:2]1[CH:6]=[C:5]([CH2:7][CH3:8])[NH:4][N:3]=1.CS[C:11](=[N:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])[CH3:12]>O1CCOCC1>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[C:14]1[N:3]2[N:4]=[C:5]([CH2:7][CH3:8])[CH:6]=[C:2]2[N:1]=[C:11]([CH3:12])[N:13]=1

Komponenten

4

Edukt 2

HCID 219910953-ethyl-1H-pyrazol-5-amineHCID 22184679N-(1-(methylthio)ethylidene)-2,4-dichlorobenzamide

Produkt 1

HCID 221846894-(2,4-Dichlorophenyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 3-amino-5-ethylpyrazole (10.3 g, 39.3 mmol) and N-(1-(methylthio)ethylidene)-2,4-dichloro-benzamide (4.0 g, 35.7 mmol) in anhydrous dioxan (20 mL) was stirred at reflux temperature under a nitrogen atmosphere for 16 h. After being cooled to ambient temperature, the reaction mix was concentrated in vacuo and the residue was treated with dichloromethane. The resulting supsension was filtered and the filtrate was concentrated in vacuo to afford an oil (1.5 g, 14% yield): NMR (CDCl3,300 MHz): δ 7.62 (d, 1H, J=8), 7.59 (d, 1H, J=2), 7.45 (dd, 1H, J=8,2), 6.42 (s, 1H), 2.82 (q, 2H, J=8), 2.73 (s, 3H), 1.30 (t, 3H, J=8).

Aufarbeitung

  1. temperatureat reflux temperature under a nitrogen atmosphere for 16 h
  2. additionthe reaction mix
  3. concentrationwas concentrated in vacuo
  4. additionthe residue was treated with dichloromethane
  5. filtrationThe resulting supsension was filtered
  6. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3550ee809b1546f6b72375e364609e96
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960583B2

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