Chlorosuccinimide → Methyl 3-(5-chloro-2-methyl-1H-imidazol-4-yl)-4-methylbenzoate

HRID 1487846노트

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HRID 1487846 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[NH:16][C:15]([CH3:17])=[N:14][CH:13]=1.C1C(=O)N([Cl:25])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Cl:25][C:13]1[NH:14][C:15]([CH3:17])=[N:16][C:12]=1[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[CH3:1])[C:6]([O:8][CH3:9])=[O:7]

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 90029434Methyl 4-methyl-3-(2-methyl-1H-imidazol-5-yl)benzoate2회

생성물 1

HCID 90030158Methyl 3-(5-chloro-2-methyl-1H-imidazol-4-yl)-4-methylbenzoate수율 82.1%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

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온도
50 °C

실험 절차

To a solution of methyl 4-methyl-3-(2-methyl-1H-imidazol-5-yl)benzoate (compound 7.1, 317 mg, 1.38 mmol) in carbon tetrachloride (30 mL) was added NCS (184 mg, 1.38 mmol). The mixture was stirred at 50° C. for 16 hours, then cooled to room temperature and washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-50% EtOAc in hexanes) to yield the title compound as a solid (300 mg, 82%). m/z (ES+) 265 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 9.55 (br s, 1H), 8.01-7.87 (m, 2H), 7.37 (d, J=7.8 Hz, 1H), 3.91 (s, 3H), 2.42 (s, 3H), 2.40 (s, 3H).

후처리

  1. temperaturecooled to room temperature
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (0-50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-c447fe4b4e78465189f50041ebc33696
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428502B2

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