HCID 178418361, compound → HCID 178432333, compound

HRID 1610838Notes

Reaction equation

HRID 1610838 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:4]=2[N:3]=1.[H][H]>>[CH3:1][C:2]1[NH:6][C:5]2[CH2:7][CH2:8][CH:9]([CH3:11])[CH2:10][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178423477HCID 178423477, compound

Product 1

HCID 178432333HCID 178432333, compound

Procedure

20.0 g (0.137 mol) of 2,5-dimethyl-1H-benzimidazole are dissolved in 150 ml glacial acid and 2.50 g Pt-Mohr catalyst are added under argon. The solution is treated with hydrogen at 80° C. and at 3 bar pressure for 72 h. The solution is filtrated over celite and washed with glacial acid. The solvent is evaporated under vacuum and a few milliliters of water are added to the residue. Sodium hydrogen solution is added to a pH of 12-14. The mixture is extracted with ethyl acetate, the organic phase is extracted with water and dried over sodium sulfate. The ethyl acetate is evaporated under pressure and the residue is dissolved in a little bit of dichlormethane. Diethylether is added and the precipitate is filtrated and washed with diethylether to yield 1.0 g (4.87% of th.).

Workup

  1. additionare added under argon
  2. filtrationThe solution is filtrated over celite
  3. washwashed with glacial acid
  4. customThe solvent is evaporated under vacuum and a few milliliters of water
  5. additionare added to the residue
  6. additionSodium hydrogen solution is added to a pH of 12-14
  7. extractionThe mixture is extracted with ethyl acetate
  8. extractionthe organic phase is extracted with water
  9. dry with materialdried over sodium sulfate
  10. customThe ethyl acetate is evaporated under pressure
  11. dissolutionthe residue is dissolved in a little bit of dichlormethane
  12. additionDiethylether is added
  13. filtrationthe precipitate is filtrated
  14. washwashed with diethylether
  15. customto yield 1.0 g (4.87% of th.)

Sources & evidence

ORD record
ord-2b97ba9c6af54e569537bbdbc03c42c3
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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