2,3-Dihydroxybutanedioic Acid → 1,2-Bis(1-methyl-1H-benzimidazol-2-yl)ethan-1,2-diol

HRID 868903Notes

Reaction equation

HRID 868903 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:10](O)(=O)[CH:11]([CH:13]([C:15](O)=O)[OH:14])[OH:12]>Cl>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:9]=[C:10]1[CH:11]([OH:12])[CH:13]([C:15]1[N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:9]=1)[OH:14]

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 78498N-Methyl-o-phenylenediamine

Product 1

HCID 52331141,2-Bis(1-methyl-1H-benzimidazol-2-yl)ethan-1,2-diolYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-Methylbenzene-1,2-diamine (13.5 g, 85.4 mmol) and tartaric acid (6.4 g, 42.6 mmol) were dissolved in 4 N aqueous HCl (100 mL), and the solution was stirred at reflux overnight. After cooling to room temperature, the precipitate was collected by vacuum filtration and re-dissolved in water (200 mL), and the pH of the resulting mixture was adjusted to 8 with aqueous NH4OH solution. The precipitate was collected by vacuum filtration and dried to give 6.86 g of the desired product, which was used for the next step without further purification. LC-MS: m/z 323 (M+H+).

Workup

  1. temperatureat reflux overnight
  2. filtrationthe precipitate was collected by vacuum filtration
  3. dissolutionre-dissolved in water (200 mL)
  4. filtrationThe precipitate was collected by vacuum filtration
  5. customdried

Sources & evidence

ORD record
ord-9d8f6ba0732d4cc4a29bef0fffde5573
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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