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Aniline → 2-[4-(4-Fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-pyrazol-1-yl]-N-phenyl-acetamide

HRID 377690
ノート
印刷プレビュー

反応式

HRID 377690 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.C([O:14][C:15](=O)[CH2:16][N:17]1[C:21]([C:22]([F:25])([F:24])[F:23])=[C:20]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[C:19]([C:33]2[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=2)=[N:18]1)C>C(Cl)Cl>[C:2]1([NH:1][C:15](=[O:14])[CH2:16][N:17]2[C:21]([C:22]([F:25])([F:23])[F:24])=[C:20]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[C:19]([C:33]3[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=3)=[N:18]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6115AnilineHCID 10227082ethyl [4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetateHCID 16682925Trimethylaluminum

生成物 1

HCID 101186862-[4-(4-Fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-pyrazol-1-yl]-N-phenyl-acetamide収率 69.6%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
25 °C

実験手順

Aniline (0.07 g, 0.75 mmol) was added to a methylene chloride solution of trimethyl aluminum (0.38 mL, 0.75 mmol, 2.0 M in hexanes) at 25° C. under nitrogen. After gas evolution had ceased (approx. 30 minutes), ethyl[4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetate (Example 8) (0.25 g, 0.5 mmol) was added and the mixture stirred for 24 hours at 25° C. The reaction was quenched with dilute aqueous HCl and extracted with two portions ethyl acetate and the extracts washed with brine, dried over MgSO4 and concentrated in vacuo. Recrystallization from chloroform/acetone gave N-phenyl-[4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetamide as a white crystalline solid (0.18 g, 68% yield). Elemental analysis for C25H19N3F4SO3Calc'd: C, 58.02, H, 3.70, N. 8.12, S, 6.20. Found: C, 57.48, H, 3.78, N, 8.03, S, 6.46.

後処理

  1. additionwas added
  2. customThe reaction was quenched with dilute aqueous HCl
  3. extractionextracted with two portions ethyl acetate
  4. washthe extracts washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from chloroform/acetone

出典と根拠

ORDレコード
ord-6cd11e3d437942c8a8fb49b870531065
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06028072

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート