Acetic Acid → 2-[1-(4-Nitrophenyl)ethylidene]malononitrile

HRID 32488

반응식

HRID 32488 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])(=O)C.[NH4+].C(O)(=O)C.[C:22](#[N:26])[CH2:23][C:24]#[N:25]>O1CCOCC1.C1(C)C=CC=CC=1.[Cl-].[Na+].O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[C:23]([C:22]#[N:26])[C:24]#[N:25])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

9

반응물 4

HCID 176Acetic AcidHCID 7487p-NitroacetophenoneHCID 8010MalononitrileHCID 517165Ammonium Acetate

생성물 1

HCID 110420862-[1-(4-Nitrophenyl)ethylidene]malononitrile

시약·촉매·용매 4

HCID 1140Toluene용매2회HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

실험 절차

p-Nitro-acetophenone (165 g/mole; 4.0 g; 24 mmoles), ammonium acetate (0.50 g) and glacial acetic acid (0.80 mL) were added to a round-bottom flask containing 20 mL toluene, and heated to reflux using a Dean-Stark trap and a reflux condenser. Separately, malononitrile (66 g/mole; 2.0 g; 30.3 mmoles) was dissolved in 5 mL dioxane and 20 mL toluene, transferred to an addition funnel and added dropwise to the heated solution of ketone. Upon completion of the addition, the system was heated for 2 hours and then cooled to room temperature. The reaction mixture was poured into 150 mL brine and 100 mL ethyl acetate. The aqueous layer was separated and washed with 50 mL ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the crude product 2-[1-(4-nitrophenyl)-ethylidene]-malononitrile (213 g/mole) was used as such in Intermediate Example 11.

후처리

  1. temperatureheated
  2. temperatureto reflux
  3. additionUpon completion of the addition
  4. temperaturethe system was heated for 2 hours
  5. customThe aqueous layer was separated
  6. washwashed with 50 mL ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-2d3178a7af6744be8777365630066edd
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427623B2

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