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Dimethyl Sulfoxide → [2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester

HRID 2352890
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HRID 2352890 반응식
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)=[CH:13][C:12]=1[N+:28]([O-:30])=[O:29])C(OCC)=O)[CH3:2].CS(C)=O.O>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)=[CH:13][C:12]=1[N+:28]([O-:30])=[O:29])[CH3:2]
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참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 59256487Diethyl 2-(2-nitro-4-(3-nitrobenzoyl)phenyl)malonate

생성물 1

HCID 86610408[2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester수율 89%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

A 2 L, 3-necked round bottomed flask equipped with a heating mantle, condenser, overhead stirrer, thermocouple, and N2(g) inlet was charged with 2-[2-Nitro-4-(3-nitro-benzoyl)-phenyl]-malonic acid diethyl ester (105 g, 0.24 mol), DMSO (1 L) and H2O (87 mL) The reaction was heated at 110° C. for 11 h. Thin layer chromatographic analysis (Hexanes/ethylacetate 6:4) indicated completion of reaction. The reaction mixture was cooled to room temperature and was diluted with ethyl acetate (4 L). The organic layer was washed with brine (3×4 L), dried over Na2SO4 and concentrated. Methyl t-butyl ether (1 L) was added to the solids and stirred. The product was filtered and washed with Methyl t-butyl ether (2×250 mL). The solids collected were dried in the vacuum oven at 45° C. for 24 hours to yield 89% of pure [2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester (77 g, 0.21 mol).

후처리

  1. customA 2 L, 3-necked round bottomed flask equipped with a heating mantle, condenser, overhead stirrer
  2. customcompletion of reaction
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washThe organic layer was washed with brine (3×4 L)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. additionMethyl t-butyl ether (1 L) was added to the solids
  8. filtrationThe product was filtered
  9. washwashed with Methyl t-butyl ether (2×250 mL)
  10. customThe solids collected
  11. customwere dried in the vacuum oven at 45° C. for 24 hours

출처 및 근거

ORD 기록
ord-06e8e9568db545888b62da2c67667ae8
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07749530B2

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