Pentane → (2-(4-Chlorophenyl)-1-(phenylsulfonyl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 70060

반응식

HRID 70060 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.CCCCC.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:40]=[C:41]([O:45][CH3:46])[C:42]=1[O:43][CH3:44])[C:37](Cl)=[O:38]>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:10]=[C:11]([C:37]([C:36]3[CH:40]=[C:41]([O:45][CH3:46])[C:42]([O:43][CH3:44])=[C:34]([O:33][CH3:32])[CH:35]=3)=[O:38])[N:12]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8003PentaneHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 497885002-(4-Chlorophenyl)-1-(phenylsulfonyl)-1H-imidazoleHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 49788802(2-(4-Chlorophenyl)-1-(phenylsulfonyl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone수율 36.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 2-(4-chlorophenyl)-1-(phenylsulfonyl)-1H-imidazole (10f) (6.0 mmol) in anhydrous THF (30 mL) at −78° C. was added 1.7 M tert-butyllithium in pentane (5.3 mL, 9.0 mmol) and stirred for 10 min. 3,4,5-Trimethoxybenzoyl chloride (7.2 mmol) was added at −78° C. and stirred for overnight. The reaction mixture was diluted with 100 mL of saturated NaHCO3 solution (aqueous) and extracted by ethyl acetate (200 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (hexane:ethyl acetate 4:1) to give a white solid. Yield: 36.8%; 1H NMR (500 MHz, CDCl3) δ 8.05 (d, J=7.5 Hz, 2H), 7.77 (t, J=7.5 Hz, 1H), 7.62 (t, J=8.0 Hz, 2H), 7.48 (s, 1H), 7.44 (d, J=9.0 Hz, 2H), 7.39 (d, J=8.5 Hz, 2H), 7.37 (s, 2H). MS (ESI): calculated for C25H21ClN2O6S, 512.1. found 513.1 [M+H]+.

후처리

  1. stirringstirred for overnight
  2. extractionextracted by ethyl acetate (200 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (hexane:ethyl acetate 4:1)
  6. customto give a white solid

출처 및 근거

ORD 기록
ord-f613d3706ed846c89d6ff52f90c5d1df
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822513B2

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