Ethanol → 1,5-Dimethylbenzimidazole

HRID 1110805ノート

反応式

HRID 1110805 の反応式
[CH3:1][N:2]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[N+:12]([O-])=O)[CH:3]=O.C(O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH3:1][N:2]1[C:5]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=2[N:12]=[CH:3]1

参加物

5

反応物 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 14856787HCID 14856787、化合物

生成物 1

HCID 129211011,5-Dimethylbenzimidazole収率 67%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

N-Methyl-N-(4-methyl-2-nitrophenyl)formamide, 20 g (103 mmols), was added to 400 ml of ethanol and a solution of sodium hydrosulfite, 54g (310 mmols) in 300ml of water was added dropwise to the mixture at 80° C. After stirring at 80° C. for 7 hours, the mixture was stirred at room temperature for further 16 hours. The solvent was distilled off under reduced pressure and 200 ml of 1N sodium hydroxide aqueous solution was added to the residue followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The resulting crystals were washed with ether to give 10.0 g (67,3%) of 1,5-dimethylbenzimidazole.

後処理

  1. stirringthe mixture was stirred at room temperature for further 16 hours
  2. distillationThe solvent was distilled off under reduced pressure and 200 ml of 1N sodium hydroxide aqueous solution
  3. additionwas added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. washThe resulting crystals were washed with ether

出典と根拠

ORDレコード
ord-b546d2d3b4ef4e3fb011ced3667a2b08
出典データセット
uspto-grants-1990_12
特許番号
US04977175

反応ノート

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