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

HRID 1698559ノート

反応式

HRID 1698559 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:12])[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(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:12][C:11]1[C:4]2[N:3]=[C:2]([O:27][C:20]3[C:21]([CH3:26])=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=3[Cl:18])[N:6]([CH3:7])[C:5]=2[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=1

参加物

6

反応物 3

HCID 11430Potassium Carbonate3 回HCID 152922,4-Dichloro-6-methylphenol3 回HCID 672730252,4-Dichloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole

生成物 1

HCID 119482864-Chloro-2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole収率 64%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A solution of 2,4-dichloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole (5.5 g, 20.2 mmol), 2,4-dichloro-6-methylphenol (10 g, 56.5 mmol) and potassium carbonate (8.4 g, 60.8 mmol) in N,N-dimethylformamide (55 mL) was heated at 100° C. for 9 h. To the mixture was added 2,4-dichloro-6-methylphenol (5 g, 28.3 mmol) and potassium carbonate (4.2 g, 30.4 mmol) and heated at 100° C. for 16 h. Additional 2,4-dichloro-6-methylphenol (5 g, 28.3 mmol) and potassium carbonate (4.2 g, 30.4 mmol) were added and heated at 100° C. for 9 h. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on NH silica gel eluting with a 12.5% ethyl acetate/n-hexane. The resulting solids were recrystallized from a 10% ethyl acetate/n-hexane to give 5.3 g (64%) of the title compound as a colorless crystal.

後処理

  1. temperatureheated at 100° C. for 9 h
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on NH silica gel eluting with a 12.5% ethyl acetate/n-hexane
  9. customThe resulting solids were recrystallized from a 10% ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-e25d4cfab0804f97aa3f5ff1b4bb6689
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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