Triethylamine → 1-(2-Hydroxyethyl)-1H-benzimidazole-7-carbonitrile

HRID 419936Notes

Reaction equation

HRID 419936 reaction equation
[NH2:1][C:2]1[C:3]([NH:10][CH2:11][CH2:12][OH:13])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH2:14](N(CC)CC)C>C(O)=O.CO>[OH:13][CH2:12][CH2:11][N:10]1[C:3]2[C:4]([C:5]#[N:6])=[CH:7][CH:8]=[CH:9][C:2]=2[N:1]=[CH:14]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 582984983-Amino-2-[(2-hydroxyethyl)amino]benzonitrile

Product 1

HCID 114467811-(2-Hydroxyethyl)-1H-benzimidazole-7-carbonitrileYield 70%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

3-amino-2-[(2-hydroxyethyl)amino]benzonitrile (38 g, crude), is dissolved in formic acid (150 ml) and stirred under reflux for 1 hour. The reaction mixture is concentrated to dryness under reduced pressure to give a dark solid. This solid is dissolved in 200 ml of methanol with heating and while still hot, 60 ml of triethylamine is added and reflux for 1 hour. The mixture is concentrated under vacuum and the precipitate is filtered and washed with water then dried to give the desired compound (27 g, 70% from intermediate 11).

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  3. customto give a dark solid
  4. temperaturewith heating
  5. temperaturereflux for 1 hour
  6. concentrationThe mixture is concentrated under vacuum
  7. filtrationthe precipitate is filtered
  8. washwashed with water
  9. customthen dried

Sources & evidence

ORD record
ord-bf002e972ef84b56a19dd2a3d7190813
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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