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

HRID 1926516Notes

Reaction equation

HRID 1926516 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 5 g of 1,2-phenylene diamine, 2.4 g of malonic acid, and 20 g of polyphosphoric acid. The mixture was heated to 180 C under nitrogen for 4 hours, and then cooled to 150 C. After the addition of 40 ml of water, the mixture was cooled to 22 C and neutralized with aqueous ammonium hydroxide. The solid was filtered and washed with water. After triturating the product in 200 ml of hot acetonitrile, the mixture was cooled to 22 C, filtered, washed with acetonitrile, and dried resulting in 2.7 g of a gray solid.

Workup

  1. temperatureThe mixture was heated to 180 C under nitrogen for 4 hours
  2. temperaturecooled to 150 C
  3. temperaturethe mixture was cooled to 22 C
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customAfter triturating the product in 200 ml of hot acetonitrile
  7. temperaturethe mixture was cooled to 22 C
  8. filtrationfiltered
  9. washwashed with acetonitrile
  10. customdried

Sources & evidence

ORD record
ord-5cbcfc092f95452da6a79b3538e3da39
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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