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

HRID 1798021노트

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HRID 1798021 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매2회

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온도
70 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-ee76062ee6064e0abc2bcf803b446e58
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343964B2

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