Hydrochloric Acid → Benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoate

HRID 1798021

Reaktionsgleichung

Reaktionsgleichung von HRID 1798021
[C:1]([CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])#[N:2].C(=O)([O-])[O-].[K+].[K+].[N+:20]([C:23]1[CH:24]=[C:25]([CH3:30])[CH:26]=[CH:27][C:28]=1Cl)([O-:22])=[O:21].Cl>CN(C=O)C.O.CCOCC>[C:1]([CH:3]([C:28]1[CH:27]=[CH:26][C:25]([CH3:30])=[CH:24][C:23]=1[N+:20]([O-:22])=[O:21])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])#[N:2]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 69764-Chloro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 560818Benzyl 2-cyanoacetate

Produkt 1

HCID 10935797Benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

benzyl cyanoacetate (3.50 g; 20 mmol) is added to a suspension of potassium carbonate (6.08 g; 44 mmol) in 5 mL of DMF. The carbonate is washed with 2 mL of DMF. A solution of 3-nitro-4-chlorotoluene (3.41 g, 20 mmol) in 5 mL of DMF is added and the resulting reaction mixture is stirred at 70° C. for 24 hours. After cooling down to ambient temperature, it is treated with a 5N aqueous solution of HCl (12.5 mL). The mixture is divided between ether (100 mL) and water (50 mL) then the organic phase is re-extracted with ether. The ethereal phases are washed with water, dried over anhydrous MgSO4, filtered under vacuum and evaporated. The residue is purified by chromatography on silica gel (eluent: CH2Cl2/pentane, 1/1) in order to produce benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoate with a yield of 75%.

Aufarbeitung

  1. washThe carbonate is washed with 2 mL of DMF
  2. customthe resulting reaction mixture
  3. temperatureAfter cooling down to ambient temperature
  4. extractionthe organic phase is re-extracted with ether
  5. washThe ethereal phases are washed with water
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered under vacuum
  8. customevaporated
  9. customThe residue is purified by chromatography on silica gel (eluent: CH2Cl2/pentane, 1/1) in order

Quellen und Nachweise

ORD-Eintrag
ord-ee76062ee6064e0abc2bcf803b446e58
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343964B2

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