p-Toluenesulfonic acid → 2-(2,5-Diphenyl-pyrrol-1-ylimino)-3-(2,5-dipyridine-3-yl-pyrrol-1-ylimino)-butane

HRID 1265295Notes

Reaction equation

HRID 1265295 reaction equation
[C:1]1([C:7]2[N:8]([N:18]=[C:19]([CH3:23])[C:20](=O)[CH3:21])[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]2[N:36]([NH2:46])[C:37]([C:40]3[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=3)=[CH:38][CH:39]=2)[CH:30]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[C:1]1([C:7]2[N:8]([N:18]=[C:19]([C:20](=[N:46][N:36]3[C:37]([C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)=[CH:38][CH:39]=[C:35]3[C:31]3[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=3)[CH3:21])[CH3:23])[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 186154692,5-Di-pyridin-3-yl-pyrrol-1-ylamineHCID 571252783-(2,5-Diphenyl-pyrrol-1-ylimino)-butan-2-one

Product 1

HCID 725005572-(2,5-Diphenyl-pyrrol-1-ylimino)-3-(2,5-dipyridine-3-yl-pyrrol-1-ylimino)-butane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A suspension of 3-(2,5-Diphenyl-pyrrol-1-ylimino)-butan-2-one (1.0 g, 3.4 mmol) in toluene (12 ml) is treated with DMF (6 ml), 2,5-di-pyridin-3-yl-pyrrol-1-ylamine (850 mg, 3.6 mmol) and p-toluene sulfonic acid (30 mg). The resulting suspension is fitted with a Dean Stark trap and heated to reflux with azeotropic removal of water in an oil bath until no starting materials remain by TLC. The solution is cooled to rt and concentrated in vacuo. The residue is purified by flash chromatography to afford 2-(2,5-diphenyl-pyrrol-1-ylimino)-3-(2,5-dipyridine-3-yl-pyrrol-1-ylimino)-butane.

Workup

  1. customThe resulting suspension is fitted with a Dean Stark trap
  2. temperatureheated
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-20de498ededb4725b7aaa9335124e3e1
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Reaction notes

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