Acetic Acid → (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-thiophen-2-yl-acetonitrile

HRID 612355

반응식

HRID 612355 반응식
[OH-].[K+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]#[N:10].[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-])=[O:12].C(O)(=O)C>CO.O>[OH:12][N:11]=[C:14]1[CH:19]=[CH:18][C:17](=[C:8]([C:4]2[S:3][CH:7]=[CH:6][CH:5]=2)[C:9]#[N:10])[CH:16]=[CH:15]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7416NitrobenzeneHCID 14797Potassium HydroxideHCID 728802-Thienylacetonitrile

생성물 1

HCID 19594042(4-Hydroxyimino-cyclohexa-2,5-dienylidene)-thiophen-2-yl-acetonitrile수율 50.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

9.5 g of KOH are dissolved in 50 ml of methanol. To the solution are added 5 g (41 mmol) of thiophene-2-acetonitrile followed by 4.2 ml (41 mmol) of nitrobenzene. After the reaction mixture is stirred at room temperature for 2 hrs, 200 ml of water are added with stirring. The resulting solution is acidified by addition of 30 ml of acetic acid in 25 ml of water, leading to a dark orange precipitate. The mixture is then filtered, and the solid is washed with a mixture of methanol and water, and methanol. The crude product is dried in air and recrystallized from toluene. 4.7 g (50%) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-thiophen-2-yl-acetonitrile are obtained in the form of a dark orange powder having a melting point of 151-155° C. (dec.).

후처리

  1. stirringwith stirring
  2. filtrationThe mixture is then filtered
  3. washthe solid is washed with a mixture of methanol and water, and methanol
  4. dry with materialThe crude product is dried in air
  5. customrecrystallized from toluene

출처 및 근거

ORD 기록
ord-56fa11f9501247e99ec0bf6f2fefe14b
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06004724

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