m-Chloroperbenzoic acid → 2-[4,4-bis(trifluoromethyl)-2-(4-fluorophenyl)-4,5-dihydro-1H-imidazol-5-ylidene]-1-(4-fluorophenyl)-1-ethanone

HRID 22305노트

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HRID 22305 반응식
[F:1][C:2]([F:29])([F:28])[C:3]([C:24]([F:27])([F:26])[F:25])([C:5]1[NH:6][C:7]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:9]=1)[NH2:4].ClC1C=CC=C(C(OO)=[O:38])C=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[F:29][C:2]([F:28])([F:1])[C:3]1([C:24]([F:25])([F:26])[F:27])[C:5](=[CH:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:38])[NH:6][C:7]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[N:4]1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acid2회HCID 516892Sodium BicarbonateHCID 10895067alpha,alpha-bis(trifluoromethyl)-4,5-bis(4-fluorophenyl)-1H-pyrrole-2-methanamine

생성물 1

HCID 540378242-[4,4-bis(trifluoromethyl)-2-(4-fluorophenyl)-4,5-dihydro-1H-imidazol-5-ylidene]-1-(4-fluorophenyl)-1-ethanone수율 20%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of α,α-bis(trifluoromethyl)-4,5-bis(4-fluorophenyl)-1H-pyrrole-2-methanamine (5.0 g, 0.012 mole) in chloroform (100 mL) was added portionwise, m-chloroperbenzoic acid (MCPBA, 4.09 g, 0.024 mole). The reaction mixture was refluxed under nitrogen for one hour. Then additional MCPBA (2.05 g, 0.012 mole) was added and the mixture was refluxed for 1 hour. The solution was cooled to room temperature and poured into saturated sodium bicarbonate (200 ml). The organic layer was washed successively with saturated sodium bicarbonate solution, 10% sodium sulfite solution, water, and saturated sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum. The residue was columned in silica gel eluted with hexane-ethyl acetate 20:1 then 10:1 to give the 2-[4,4-bis(trifluoromethyl)-2-(4-fluorophenyl)-4,5-dihydro-1H-imidazol-5-ylidene]-1-(4-fluorophenyl)-1-ethanone (1.02 g, 20%) as a yellow solid: mp 121°-123°; MS m/e 435 (M+ +H); 1H NMR (CDCl3 /TMS) δ 6.73(s,1H,C=CH), 7.17-7.30(m,4H,Harom), 8.00-8.10(m,4H,Harom), 11.80(s,1H,NH). Another product, N[2-(4-fluorophenyl)-4,5-dihydro-1-methyl-5,5-bis(trifluoromethyl)-1H-imidazol-5-yl]-N-methylacetamide (2.09 g, 56%) was also isolated as a solid: mp 114°-115°; MS m/e 437 (M+ +H); 1H NMR (CDCl3 /TMS) δ 2.57(s,2H,NH2), 3.87(s,1H,NH), 6.77(s,1H,C=CH), 6.90-7.03(m,4H,Harom), 7.23-7.40(m, 2H,Harom), 7.15-7.17(m,2H,Harom).

후처리

  1. temperatureThe reaction mixture was refluxed under nitrogen for one hour
  2. temperaturethe mixture was refluxed for 1 hour
  3. washThe organic layer was washed successively with saturated sodium bicarbonate solution, 10% sodium sulfite solution, water, and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. washeluted with hexane-ethyl acetate 20:1

출처 및 근거

ORD 기록
ord-7056b392e99343b7abedb3db3bed6424
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428041

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