Ammonia → 2,5'-Bi-1H-benzimidazole, 1-methyl-2'-propyl-

HRID 2292717Notes

Reaction equation

HRID 2292717 reaction equation
S(O)(O)(=O)=O.[CH2:6]([C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18](O)=O)[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH2:7][CH3:8].C([C:24]1[NH:25][C:26]2[CH:32]=[C:31](C(O)=O)[CH:30]=[CH:29][C:27]=2[N:28]=1)CC.Cl.Cl.CNC1C=CC=CC=1N.N>O>[CH2:6]([C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]3[N:25]([CH3:24])[C:26]4[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=4[N:28]=3)[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 91296N-Methyl-o-phenylenediamine dihydrochlorideHCID 856442212-n-Propyl-benzimidazole-5-carboxylic acid-hemisulphate

Product 1

HCID 104694762,5'-Bi-1H-benzimidazole, 1-methyl-2'-propyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.7 g (25 mMol) of 2-n-propyl-benzimidazole-5-carboxylic acid-hemisulphate and 4.9 g (25 mMol) of 2-methylaminoaniline-dihydrochloride in 200 g of polyphosphoric acid is stirred for 5 hours at 150° C., then poured onto 600 ml of water and made alkaline with concentrated ammonia whilst cooling with ice. The resulting solution is extracted three times with 200 ml of ethyl acetate, the crude product thus obtained is purified by column chromatography (300 g of silica gel; eluant: methylene chloride/methanol=15:1).

Workup

  1. temperaturewhilst cooling with ice
  2. extractionThe resulting solution is extracted three times with 200 ml of ethyl acetate

Sources & evidence

ORD record
ord-859b6e201805402fb07780c425093ede
Source dataset
uspto-grants-1997_11
Patent number
US05684029

Reaction notes

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