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

HRID 1061545

反応式

HRID 1061545 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3550ee809b1546f6b72375e364609e96
出典データセット
uspto-grants-2005_11
特許番号
US06960583B2

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