Hydrochloric Acid → HCID 21861210, compound

HRID 348514Notes

Reaction equation

HRID 348514 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[C:8]1([NH2:15])[CH:13]=[CH:12][CH:11]=CC=1N.Cl.[OH-:17].[Na+].[CH2:19]([OH:21])[CH3:20]>C(Cl)(Cl)Cl>[CH2:19]([O:21][C:11](=[O:17])[CH2:12][CH2:13][CH2:8][CH2:7][C:6]1[NH:15][C:8]2[CH:13]=[CH:12][CH:11]=[CH:5][C:4]=2[N:3]=1)[CH3:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 14798Sodium Hydroxide

Product 1

HCID 21861210HCID 21861210, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

696 μl (5.0 mmol) of triethylamine and 893 mg (5.0 mmol) of methyladipochloride were dropped into 10 ml of a chloroform solution containing 540 mg (5.0 mmol) of orthophenylenediamine followed by stirring for 12 hours at room temperature. 20 ml of ethanol and 4 ml of concentrated hydrochloric acid were then added followed by stirring for 10 hours while heating and refluxing. The reaction solution was then neutralized using 5 M aqueous sodium hydroxide solution followed by extraction with ethyl acetate. After washing with water and concentrating under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate only) to obtain 359 mg of 5-(benzimidazole-2-yl)pentanoate ethyl ester (yield: 30%).

Workup

  1. stirringby stirring for 10 hours
  2. temperaturewhile heating
  3. temperaturerefluxing
  4. extractionfollowed by extraction with ethyl acetate
  5. washAfter washing with water
  6. concentrationconcentrating under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate only)

Sources & evidence

ORD record
ord-b5c7ec9212a343b591fb0dba6ffaa5db
Source dataset
uspto-grants-2007_02
Patent number
US07176320B2

Reaction notes

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