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N-methyl-2-pyrrolidone → N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-1,4-dimethyl-1H-benzimidazol-2-amine

HRID 1698565
ノート
印刷プレビュー

反応式

HRID 1698565 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]([CH3:12])[C:4]=2[N:3]=1.[Cl:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:22]([NH2:23])=[C:21]([O:27][CH3:28])[CH:20]=1.CN1CCCC1=O>O>[Cl:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:22]([NH:23][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=[C:11]([CH3:12])[C:4]=3[N:3]=2)=[C:21]([O:27][CH3:28])[CH:20]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 591919724-Chloro-2-methoxy-6-methylanilineHCID 672727562-Chloro-7-(1-ethylpropyl)-1,4-dimethyl-1H-benzimidazole

生成物 1

HCID 11977539N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-1,4-dimethyl-1H-benzimidazol-2-amine収率 34.4%

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-chloro-7-(1-ethylpropyl)-1,4-dimethyl-1H-benzimidazole (100 mg, 0.399 mmol), 4-chloro-2-methoxy-6-methylaniline (205 mg, 1.20 mmol) and 1-methyl-2-pyrrolidone (0.2 mL) was stirred at 120° C. for 2 days under nitrogen atmosphere. The mixture was diluted with water and extracted with ethyl acetate, washed with brine. The organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1-1:1) and crystallized from iso-propanol to afford the title compound as colorless crystals (53 mg, 34%).

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 column chromatography on silica gel (n-hexane:ethyl acetate=10:1-1:1)
  6. customcrystallized from iso-propanol

出典と根拠

ORDレコード
ord-240750d60b23439c8a1565af64a9d86c
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163935B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート