O-Phenylenediamine → HCID 21273450, compound

HRID 1382932Notes

Reaction equation

HRID 1382932 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](O)=O)=[CH:13][CH:12]=1)#[N:10].C(=O)([O-])O.[Na+]>O>[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[N:8]=2)=[CH:13][CH:12]=1)#[N:10]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 795874-Cyanophenylacetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 21273450HCID 21273450, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30 g (0.277 mol) of o-phenylenediamine and 150 g of polyphosphoric acid ester (ppE) is heated to 120°. When the diamine has dissolved, 33 g (0.205 mol) of p-cyanophenylacetic acid are added thereto in one portion and the mixture is heated to 120° for a further 20 minuIes. After cooling to room temperature the viscous mass is treated with about 1 l of water and made weakly basic with solid sodium hydrogen carbonate. The mixture is extracted with methylene chloride and the extract is washed with water, dried over sodium sulphate and evaporated to dryness. Recrystallization of the residue from methylene chloride/ethyl acetate gives 29 g (60%) of 2-(p-cyanobenzyl)benzimidazole, m.p. 201°-203°, as a colourless crystalline powder.

Workup

  1. temperatureis heated to 120°
  2. temperaturein one portion and the mixture is heated to 120° for a further 20 minuIes
  3. extractionThe mixture is extracted with methylene chloride
  4. washthe extract is washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness
  7. customRecrystallization of the residue from methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-4fba642323d540a4b396ea2fa971648c
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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