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N,N-Diethylaniline → 3-(4-Chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

HRID 366311
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HRID 366311 반응식
C(N(CC)[C:4]1[CH:9]=CC=C[CH:5]=1)C.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])=[C:15]([O:32]CC#C)[CH:14]=1.[F-].[Cs+]>O>[Cl:12][C:13]1[C:14]2[CH:5]=[C:4]([CH3:9])[O:32][C:15]=2[C:16]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[N:21]([CH3:30])[C:20]2=[O:31])=[CH:17][CH:18]=1
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참가 물질

5

반응물 3

HCID 7061N,N-DiethylanilineHCID 25953Cesium fluorideHCID 232891823-(4-Chloro-2-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil

생성물 1

HCID 232891903-(4-Chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil수율 35%

시약·촉매·용매 1

HCID 962Water용매

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온도
185 °C

실험 절차

200 ml of N,N-diethylaniline was added to 20.0 g (55.8 mmol) of 3-(4-chloro-2-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil and 17.0 g (112 mmol) of cesium fluoride, followed by stirring at 180 to 190° C. for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 7.0 g (yield: 35.0%) of the desired product as white crystals. Melting point: 206-207° C.

후처리

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water
  4. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThen, the obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-29162f684be145f08ddef634d4414c6b
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06130187

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