Sodium Bicarbonate → N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazol-2-amine

HRID 1698607ノート

反応式

HRID 1698607 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]([F:15])([F:14])[F:13])[C:4]=2[N:3]=1.[Cl:21][C:22]1[CH:28]=[C:27]([CH3:29])[C:25]([NH2:26])=[C:24]([O:30][CH3:31])[CH:23]=1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[Cl:21][C:22]1[CH:28]=[C:27]([CH3:29])[C:25]([NH:26][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:9][CH:10]=[C:11]([C:12]([F:13])([F:14])[F:15])[C:4]=3[N:3]=2)=[C:24]([O:30][CH3:31])[CH:23]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 591919724-Chloro-2-methoxy-6-methylanilineHCID 672728702-Chloro-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazole

生成物 1

HCID 58012438N-(4-Chloro-2-methoxy-6-methylphenyl)-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazol-2-amine収率 34%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone触媒

反応条件

温度
110 °C

実験手順

A mixture of 2-chloro-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazole (290 mg, 0.95 mmol), 4-chloro-2-methoxy-6-methylaniline (491 mg, 2.86 mmol) and N-methyl-2-pyrrolidinone (3 drops) was heated at 110° C. for 72 h. Aqueous saturated sodium bicarbonate was added to the residue and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel with a 10% ethyl acetate/n-hexane and recrystallized from diisopropylether/n-hexane to give 140 mg (0.32 mmol, 34%) 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 chromatography on silica gel with a 10% ethyl acetate/n-hexane
  6. customrecrystallized from diisopropylether/n-hexane

出典と根拠

ORDレコード
ord-69aa83ef91b243eb8493850b85b3c0e6
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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