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Acetic Acid → 3-chloro-2-((E)-nitropropenyl)thiophene

HRID 450703
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인쇄 미리보기

반응식

HRID 450703 반응식
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=O.[N+:9]([CH2:12][CH3:13])([O-:11])=[O:10].C([O-])(=O)C.[NH4+].C(O)(=O)C>C(OC(=O)C)C>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[CH:7]=[CH:13]/[CH2:12][N+:9]([O-:11])=[O:10]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 27358253-Chlorothiophene-2-carbaldehyde

생성물 1

HCID 684982433-chloro-2-((E)-nitropropenyl)thiophene

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

In a sulfonation flask, a mixture containing 11.7 g (0.08 mol) 3-chlorothiophene-2-carbaldehyde, 48 g (0.64 mol) nitroethane, 15.4 g (0.2 mol) ammoniumacetate and 160 ml acetic acid is heated at 90° C. for 5 hours. After cooling ethylacetate is added and the organic phase washed three times with water. The organic phase is dried over sodium sulphate and after filtration the organic solvent is distilled off in a water jet vacuum. The residue is purified by column chromatography over silicagel (eluent: ethylacetate/heptane 1:5). Yield: 10.8 g (67% of theory) of a colourless oil (1H-NMR: 2.57/s/3H, 7.12/d/1H, 7.62/d/1H, 8.45/s/1H).

후처리

  1. additionis added
  2. washthe organic phase washed three times with water
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationafter filtration the organic solvent
  5. distillationis distilled off in a water jet vacuum
  6. customThe residue is purified by column chromatography over silicagel (eluent: ethylacetate/heptane 1:5)

출처 및 근거

ORD 기록
ord-6354ab9964f442548c4b7335e0d66d23
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486986B2

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