Succinic Acid → 2,2'-ethane-1,2-diylbis(1H-benzimidazole)

HRID 1970697Notes

Reaction equation

HRID 1970697 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9](O)(=O)[CH2:10][CH2:11][C:12](O)=O>Cl>[CH2:11]([C:12]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1)[CH2:10][C:9]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 7243O-Phenylenediamine

Product 1

HCID 2543202,2'-ethane-1,2-diylbis(1H-benzimidazole)

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a flask were added 3 g of 1,2-phenylene diamine, 1.6 g of succinic acid, and 30 ml of 4M hydrochloric acid. The mixture was heated to reflux under nitrogen for 22 hours, and then cooled to 22 C. The solid was filtered, washed with a little water and dissolved in a warm mixture of 30 ml of acetone and 40 ml of water. Enough ammonium hydroxide was added to basify the mixture, and after cooling to 22 C, the product was filtered and washed with 20 ml of 50% acetone and dried, resulting in a light pink solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen for 22 hours
  3. temperaturecooled to 22 C
  4. filtrationThe solid was filtered
  5. washwashed with a little water
  6. dissolutiondissolved in a warm mixture of 30 ml of acetone and 40 ml of water
  7. additionEnough ammonium hydroxide was added
  8. temperatureafter cooling to 22 C
  9. filtrationthe product was filtered
  10. washwashed with 20 ml of 50% acetone
  11. customdried
  12. customresulting in a light pink solid

Sources & evidence

ORD record
ord-196c586fd5404c17b7d05f9fb6356a21
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

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