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

HRID 1061545

반응식

HRID 1061545 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3550ee809b1546f6b72375e364609e96
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960583B2

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