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Bromoacetonitrile → 1-cyanomethyl-4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazole

HRID 1080489
ノート
印刷プレビュー

反応式

HRID 1080489 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)=[N:10][NH:11][C:12]=2[C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1.Br[CH2:28][C:29]#[N:30]>C1(C)C=CC=CC=1>[C:29]([CH2:28][N:11]1[C:12]([C:13]([F:16])([F:14])[F:15])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:9]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:19][CH:18]=2)=[N:10]1)#[N:30]
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

4

反応物 2

HCID 11534BromoacetonitrileHCID 153802224-(4-Fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-5-trifluoromethyl-1H-pyrazole

生成物 1

HCID 153802251-cyanomethyl-4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazole収率 11%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
190 °C

実験手順

A mixture of 4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazole (Example 1, step 3)(0.10 g), 4.2 g of bromoacetonitrile and 3 mL of toluene was heated at reflux for 2 hours. Toluene was distilled off and the mixture was heated at 190° C. for 24 hours. The reaction mixture was diluted with methylene chloride and filtered through silica gel. The filtrate was concentrated in vacuo and the residue was purified by HPLC (30% ethyl acetate-hexane). The second fraction eluted with 40% ethyl acetate-hexane yielding 1-cyanomethyl-4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazole (12 mg, 11%): mp 192°-194° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. distillationToluene was distilled off
  4. additionThe reaction mixture was diluted with methylene chloride
  5. filtrationfiltered through silica gel
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by HPLC (30% ethyl acetate-hexane)
  8. washThe second fraction eluted with 40% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-df500d841e3f426b8b5feb1672d54095
出典データセット
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05580985

反応ノート

読み込み中…

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