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

HRID 32468

반응식

HRID 32468 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=O.[CH2:13]([C:16]#[N:17])[C:14]#[N:15].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1.[Cl-].[Na+].O.C(OCC)(=O)C>[C:14]([C:13]([C:16]#[N:17])=[C:2]([C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1)[CH3:1])#[N:15]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

4Nitro acetophenone (2.0 g, 12.1 mmoles, 1 eq) and malonodinitrile (2.4 g, 36.3 mmoles, 3 eq) were dissolved in 20 mL of anhydrous toluene. To the solution were added glacial acetic acid (0.40 mL, 7.0 mmoles, 0.19 eq) and ammonium acetate (0.26 g, 3.3 mmoles, 0.09 eq). The system was heated to reflux using a Dean-Stark trap and a condenser. After 1 hour, the reaction mixture was cooled to room temperature and poured into brine (50 mL) and ethyl acetate (100 mL). The aqueous layer was washed with 3×10 mL ethyl acetate. The combined organic layers were washed with 50 mL brine, dried over anhydrous sodium sulfate and concentrated to dryness. The dark residue was partially purified using a silica plug (40% ethyl acetate-hexane) affording crude 1,1-dicyano-2-(4-nitrophenyl)-propene. The product was used as such in the next step. TLC (40% ethyl acetate-hexane)=0.61. LC-MS (m/e)=214.2 (MH+).

후처리

  1. temperatureThe system was heated
  2. temperatureto reflux
  3. washThe aqueous layer was washed with 3×10 mL ethyl acetate
  4. washThe combined organic layers were washed with 50 mL brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe dark residue was partially purified

출처 및 근거

ORD 기록
ord-6d008957c3f242c8bb72a9cb85c950bb
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427623B2

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