p-Toluenesulfonic acid → (4-amino-2-methyl-5-phenyl-1H-pyrrol-3-yl)-phenylmethanone

HRID 2397529Notes

Reaction equation

HRID 2397529 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]#[N:4].[C:11]([CH2:19][C:20](=O)[CH3:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O-]CC.[Na+]>C(O)C.C1C=CC=CC=1>[NH2:4][C:3]1[C:19]([C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:20]([CH3:21])[NH:1][C:2]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7166BenzoylacetoneHCID 408382-Amino-2-phenylacetonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 3042143(4-amino-2-methyl-5-phenyl-1H-pyrrol-3-yl)-phenylmethanone

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

2-Amino-2-phenyl-acetonitrile (0.04 mole) and benzoyl acetone (0.04 mole) are refluxed for four hours in 30 ml. of anhydrous benzene in the presence of 100 mg. of p-toluenesulfonic acid. After cooling the reaction mixture is filtered and the solvent is evaporated off to give an oily residue which is dissolved in an ethanol solution containing sodium ethoxide (0.041 mole) and the mixture is allowed to stand for 12 hours at the room temperature. The solid precipitate which forms is recovered by filtration.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationis filtered
  3. customthe solvent is evaporated off
  4. customto give an oily residue which
  5. filtrationThe solid precipitate which forms is recovered by filtration

Sources & evidence

ORD record
ord-708deb1f080b494f8f9119208f0d1642
Source dataset
uspto-grants-1977_05
Patent number
US04022766

Reaction notes

Loading…