Dimethylformamide → Methyl 2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate

HRID 1698592ノート

反応式

HRID 1698592 の反応式
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:4]=2[N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH3:30])[C:25]([OH:29])=[C:26]([Cl:28])[CH:27]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(=O)(O)[O-].[Na+]>[Cl:28][C:26]1[CH:27]=[C:22]([Cl:21])[CH:23]=[C:24]([CH3:30])[C:25]=1[O:29][C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:4]=2[N:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 152922,4-Dichloro-6-methylphenolHCID 67273217Methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate

生成物 1

HCID 58012435Methyl 2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate収率 83.1%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
110 °C

実験手順

A mixture of methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate (1.15 g, 3.90 mmol), 4,6-dichloro-o-cresol (2.07 g, 11.70 mmol), potassium carbonate (2.16 g, 15.60 mmol) and N,N-dimethylformamide (15 ml) was heated at 110° C. for 5 h. The residue was diluted with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on alumina with a 15% ethyl acetate/n-hexane to give 1.41 g (3.24 mmol, 83%) of the title compound as a white powder.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on alumina with a 15% ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-01352fdf1a0a4a9f9656d47917b3ec6d
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

読み込み中…