2-Amino-4,6-dimethylpyridine → N-(4,6-dimethyl-2-pyridyl)-1-(N,N-dimethylsulfamoyl)-5,6-dimethoxybenzimidazole-2-carboxamide

HRID 476895ノート

反応式

HRID 476895 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[H-].[Na+].[CH3:12][N:13]([CH3:35])[S:14]([N:17]1[C:21]2[CH:22]=[C:23]([O:28][CH3:29])[C:24]([O:26][CH3:27])=[CH:25][C:20]=2[N:19]=[C:18]1[C:30](OCC)=[O:31])(=[O:16])=[O:15].[Cl-].[NH4+]>CS(C)=O>[CH3:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([NH:1][C:30]([C:18]2[N:17]([S:14](=[O:16])(=[O:15])[N:13]([CH3:35])[CH3:12])[C:21]3[CH:22]=[C:23]([O:28][CH3:29])[C:24]([O:26][CH3:27])=[CH:25][C:20]=3[N:19]=2)=[O:31])[CH:7]=1

参加物

6

反応物 4

HCID 215072-Amino-4,6-dimethylpyridineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 143712791-(N,N-dimethylsulfamoyl)-2-ethoxycarbonyl-5,6-dimethoxybenzimidazole

生成物 1

HCID 19837071N-(4,6-dimethyl-2-pyridyl)-1-(N,N-dimethylsulfamoyl)-5,6-dimethoxybenzimidazole-2-carboxamide収率 67.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

In a dry argon atmosphere, 2-amino-4,6-dimethyl pyridine (4.0 g) was dissolved in dry DMSO (30 ml), 60% sodium hydride (1.30 g) was added and stirred at room temperature for 1 hr. A solution of 1-(N,N-dimethylsulfamoyl)-2-ethoxycarbonyl-5,6-dimethoxybenzimidazole (6.56 g) in DMSO (15 ml) was added dropwise while cooling and stirred at room temperature for 2 hrs. The reaction solution was poured into aqueous saturated ammonium chloride solution and extracted with benzene. The residue obtained by distilling off the solvent was purified by column chromatography on silica gel to obtain N-(4,6-dimethyl-2-pyridyl)-1-(N,N-dimethylsulfamoyl)-5,6-dimethoxybenzimidazole-2-carboxamide (5.40 g). This compound was dissolved in THF (250 ml), and then water (70 ml) and conc. hydrochloric acid (7 ml) were added allowed to react overnight at room temperature under agitation. The reaction solution was neutralized with ammonia water, THF was distilled off and the precipitated crystals were filtered off. The crystals obtained was recrystallized from chloroform/methanol to give the title compound (3.45 g).

後処理

  1. temperaturewhile cooling
  2. stirringstirred at room temperature for 2 hrs
  3. extractionextracted with benzene
  4. customThe residue obtained
  5. distillationby distilling off the solvent
  6. customwas purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-72fd3f00422f46fc95812279082e5225
出典データセット
uspto-grants-1989_12
特許番号
US04886803

反応ノート

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