Ethanol → HCID 12921101, compound

HRID 1110805Notes

Reaction equation

HRID 1110805 reaction equation
[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

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 14856787HCID 14856787, compound

Product 1

HCID 12921101HCID 12921101, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b546d2d3b4ef4e3fb011ced3667a2b08
Source dataset
uspto-grants-1990_12
Patent number
US04977175

Reaction notes

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