Dimethylformamide → Ethyl 2-[(3,5-dichloro-6-fluoropyridin-2-yl)oxy]propanoate

HRID 1448410노트

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HRID 1448410 반응식
[Na].[Cl:2][C:3]1[C:4]([OH:11])=[N:5][C:6]([F:10])=[C:7]([Cl:9])[CH:8]=1.CN(C)C=O.Br[CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C.O>[CH2:22]([O:21][C:19](=[O:20])[CH:18]([O:11][C:4]1[C:3]([Cl:2])=[CH:8][C:7]([Cl:9])=[C:6]([F:10])[N:5]=1)[CH3:24])[CH3:23]

참가 물질

7

반응물 4

HCID 6228Dimethylformamide2회HCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 178517852HCID 178517852, 화합물

생성물 1

HCID 20379580Ethyl 2-[(3,5-dichloro-6-fluoropyridin-2-yl)oxy]propanoate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

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온도
118 °C

실험 절차

A solution was prepared by dissolving 1.84 grams (0.08 mole) of sodium metal in 140 milliliters of 28 percent ethanol. To this solution was added 14.6 grams (0.08 mole) of 3,5-dichloro-6-fluoro-2-pyridinol. The solution was warmed and 60 milliliters of N,N-dimethylformamide was added thereto. The solution was further heated to remove about 3/4 of the ethanol. To the remaining solution was added 15.5 grams (0.85 mole) of ethyl bromopropionate followed by an additional 40 milliliters of N,N-dimethylformamide. The mixture was refluxed at 118° C. for 20 minutes, cooled and poured into water. The mixture was extracted with hexane and the hexane thereafter removed by evaporation. The residue was distilled under reduced pressure and the ethyl[2-(3,5-dichloro-6-fluoro-2-pyridyloxy)]propionate was recovered as an oil in a yield of 17.7 grams (78.3 percent of theoretical) and had a boiling point at 2.4 millimeters of mercury at 127° C. Upon analysis, the product was found to have carbon, hydrogen, chlorine and nitrogen contents of 42.0, 3.1, 25.1 and 5.2 percent, respectively, as compared with the theoretical contents of 42.6, 3.6, 25.1 and 4.9 percent, respectively, calculated for the above named compound.

후처리

  1. customA solution was prepared
  2. temperatureThe solution was warmed
  3. temperatureThe solution was further heated
  4. customto remove about 3/4 of the ethanol
  5. temperaturecooled
  6. extractionThe mixture was extracted with hexane
  7. customthe hexane thereafter removed by evaporation
  8. distillationThe residue was distilled under reduced pressure
  9. customthe ethyl[2-(3,5-dichloro-6-fluoro-2-pyridyloxy)]propionate was recovered as an oil in a yield of 17.7 grams (78.3 percent of theoretical)
  10. customat 127° C

출처 및 근거

ORD 기록
ord-e014fa1b3f55412ba8704707ea277f91
출처 데이터셋
uspto-grants-1979_12
특허 번호
US04180395

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