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Potassium Carbonate → 3-(1-cyano-1-methylethyl)-N-[3-(2-cyano-4-nitrophenoxy)phenyl]benzamide

HRID 455160
ノート
印刷プレビュー

反応式

HRID 455160 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[C:13]([C:15]([C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)=[O:22])([CH3:17])[CH3:16])#[N:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:13]([C:15]([C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:8]2[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=2[C:1]#[N:2])[CH:25]=1)=[O:22])([CH3:17])[CH3:16])#[N:14]
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 11430Potassium CarbonateHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 573868253-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide

生成物 1

HCID 668105993-(1-cyano-1-methylethyl)-N-[3-(2-cyano-4-nitrophenoxy)phenyl]benzamide収率 94%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a solution of 3-cyano-4-fluoronitrobenzene (1.76 g, 10.5 mmol) and 3-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide (2.97 g, 10.5 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (2.17 g, 15.7 mmol), and the mixture was stirred at 70° C. for 12 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off, water (100 ml) was added to the filtrate, and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated brine (100 mL×2), dried over anhydrous sodium sulfate, and insoluble material was filtered off. The obtained organic layer was purified by basic silica gel column chromatography (eluate: ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (4.21 g, 94%) as a yellow oil.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationinsoluble material was filtered off
  3. additionwater (100 ml) was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate (200 mL)
  5. washThe organic layer was washed with saturated brine (100 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate, and insoluble material
  7. filtrationwas filtered off
  8. customThe obtained organic layer was purified by basic silica gel column chromatography (eluate: ethyl acetate)
  9. concentrationthe obtained solution was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-0500a04f6eb34a03ae243c3c67125a96
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08497274B2

反応ノート

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