Potassium Carbonate → 2-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole

HRID 1698583ノート

反応式

HRID 1698583 の反応式
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=[C:11](Cl)[C:4]=2[N:3]=1.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[OH:27].[C:28](=O)([O-])[O-:29].[K+].[K+].CN1CCCC1=O>O>[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[O:27][C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=[C:11]([O:29][CH3:28])[C:4]=2[N:3]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 152922,4-Dichloro-6-methylphenolHCID 672730252,4-Dichloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole

生成物 1

HCID 119776482-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole収率 36%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2,4-dichloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole (200 mg, 0.750 mmol), 2,4-dichloro-6-methylphenol (398 mg, 2.25 mmol), potassium carbonate (311 mg, 2.25 mmol) and 1-methyl-2-pyrrolidone (0.5 ml) was stirred at 120° C. for 12 h under nitrogen atmosphere. The mixture was diluted with water, extracted with ethyl acetate, and washed with brine. The organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica gel with a 2-30% ethyl acetate/n-hexane gradient mixture and crystallized from methanol to afford the title compound as colorless crystals (109 mg, 36%).

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel with a 2-30% ethyl acetate/n-hexane gradient mixture
  6. customcrystallized from methanol

出典と根拠

ORDレコード
ord-2019e300a86a43f1bfde48e061e0acc8
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

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