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

HRID 612357

반응식

HRID 612357 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매2회

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-92e941ce88e042f59ba3d78a7e2be694
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06004724

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