2,5-Dimethylaniline → n-(2,5-Dimethylphenyl)-n-{4-[2-(4-fluorophenyl)-2-oxoethyl]phenyl}urea

HRID 1371022노트

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HRID 1371022 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[CH2:9][C:10]2[CH:18]=[CH:17][C:13](C(O)=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CN(C1C2C([N:33]([CH3:35])C)=CC=CC=2C=CC=1)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.[CH3:53][C:54]1[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][C:55]=1[NH2:56]>C(#N)C>[CH3:53][C:54]1[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][C:55]=1[N:56]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:19])=[CH:18][CH:17]=1)[C:35]([NH2:33])=[O:43]

참가 물질

6

반응물 4

HCID 72592,5-DimethylanilineHCID 88675Proton spongeHCID 199401P,P-Diphenylphosphinic azideHCID 185102554-[2-(4-Fluorophenyl)-2-oxoethyl]benzoic acid

생성물 1

HCID 18510233n-(2,5-Dimethylphenyl)-n-{4-[2-(4-fluorophenyl)-2-oxoethyl]phenyl}urea

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoic acid (0.100 g, 0.387 mmol) in acetonitrile was added proton sponge ((0.083 g) and diphenylphosphoryl azide (0.106 g). The reaction mixture was refluxed for 30 minutes. 2,5-dimethyl aniline (0.047 g, 0.388 mmol) was added and the mixture was refluxed another 30 minutes. The reaction was quenched with HCl 1 M and extracted with ethyl acetate, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified using flash chromatography eluting with hexane/ethyl acetate 40% to give (0.052 g) of the title compound.

후처리

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. temperaturethe mixture was refluxed another 30 minutes
  3. customThe reaction was quenched with HCl 1 M
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified
  9. washeluting with hexane/ethyl acetate 40%

출처 및 근거

ORD 기록
ord-72d4cbd6606a4cda93c73c9c3908ad8e
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583126B2

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