Ethanol → 1,5-Dimethylbenzimidazole

HRID 1110805노트

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HRID 1110805 반응식
[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

참가 물질

5

반응물 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 14856787HCID 14856787, 화합물

생성물 1

HCID 129211011,5-Dimethylbenzimidazole수율 67%

시약·촉매·용매 1

HCID 962Water용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b546d2d3b4ef4e3fb011ced3667a2b08
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04977175

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