Malonic Acid → 2,2'-methylenebis(1h-benzimidazole)

HRID 1471212Notes

Reaction equation

HRID 1471212 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][C:11](O)=O.[OH-].[NH4+:17]>O>[CH2:10]([C:11]1[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:17]=1)[C:9]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 7243O-PhenylenediamineHCID 14923Ammonium Hydroxide

Product 1

HCID 2609682,2'-methylenebis(1h-benzimidazole)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask were added 20 g polyphosphoric acid. After heating to 90 C under nitrogen, a mixture of 5.0 g 1,2-phenylenediamine and 2.4 g malonic acid were added. The reaction mixture was heated to 180 C for 4 hours, then cooled to 150 C and poured into 40 ml water. The mixture was basified with aqueous ammonium hydroxide. After cooling to 5 C, the product was filtered off and washed with water. The solid was reslurried in 200 ml hot acetonitrile, cooled, filtered and dried leaving 2.7 g of a gray solid.

Workup

  1. temperatureAfter heating to 90 C under nitrogen
  2. additionwere added
  3. temperatureThe reaction mixture was heated to 180 C for 4 hours
  4. temperaturecooled to 150 C
  5. temperatureAfter cooling to 5 C
  6. filtrationthe product was filtered off
  7. washwashed with water
  8. temperaturecooled
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-a185ec5d944e46579746bbf9a6340ae0
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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