Glycine → 1H-Benzimidazole-2-methanamine

HRID 1725599Notes

Reaction equation

HRID 1725599 reaction equation
[NH2:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[NH2:9][CH2:10][C:11](O)=O>Cl>[NH2:9][CH2:10][C:11]1[NH:1][C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[N:4]=1

Participants

4

Reactant 2

HCID 750GlycineHCID 7243O-Phenylenediamine

Product 1

HCID 1458201H-Benzimidazole-2-methanamineYield 59.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-aminoaniline (27 g, 0.25 mol), glycine (27.7 g, 0.37 mol) and 250 ml of 5.5M hydrochloric acid is refluxed for 30 hours and then stored in a refrigerator for 24 hours. The precipitate formed is filtered off with suction and then taken up in 400 ml of methanol and treated with carbon black. The mixture is filtered and the solvent is removed to give 22 g (49%) of a white solid.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off with suction
  3. additiontreated with carbon black
  4. filtrationThe mixture is filtered
  5. customthe solvent is removed

Sources & evidence

ORD record
ord-7e7c3576977a4a668f827269912b0b55
Source dataset
uspto-grants-2009_02
Patent number
US07491733B2

Reaction notes

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