Acetic Acid → (5-Hydroxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile

HRID 612357

反応式

HRID 612357 の反応式
[OH-].[K+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)([O-])=[O:13].C(O)(=O)C>CO.O>[OH:13][N:12]=[C:15]1[S:16][C:17](=[C:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:10]#[N:11])[CH:18]=[CH:19]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8794PhenylacetonitrileHCID 11866Thiophene, 2-nitro-HCID 14797Potassium Hydroxide

生成物 1

HCID 59115159(5-Hydroxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile収率 38%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒2 回

実験手順

14 g of KOH are dissolved in 50 ml of methanol. To the solution are added 7.1 ml (62 mmol) of phenylacetonitrile followed by 10 g (62 mmol) of 2-nitrothiophene dissolved in 30 ml of methanol. After the reaction mixture is stirred in the ice bath for 10 min, 200 ml of water are added with stirring. The resulting solution is acidified by addition of 55 ml of acetic acid in 50 ml of water, and extracted with ethyl acetate. The organic phase is washed with sodium chloride solution, and dried over MgSO4. After the solvent is distilled off, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3), and recrystallization from toluene. 5.3 g (38%) of (5-Hydroxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile are obtained in the form of orange crystals having a melting point of 165° C. (dec.).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with sodium chloride solution
  3. dry with materialdried over MgSO4
  4. distillationAfter the solvent is distilled off
  5. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3), and recrystallization from toluene

出典と根拠

ORDレコード
ord-92e941ce88e042f59ba3d78a7e2be694
出典データセット
uspto-grants-1999_12
特許番号
US06004724

関連ノート

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