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

HRID 1487846ノート

反応式

HRID 1487846 の反応式
[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]

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 90029434Methyl 4-methyl-3-(2-methyl-1H-imidazol-5-yl)benzoate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c447fe4b4e78465189f50041ebc33696
出典データセット
uspto-grants-2016_08
特許番号
US09428502B2

反応ノート

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