p-Toluenesulfonic acid monohydrate → HCID 11463589, compound

HRID 1296358Notes

Reaction equation

HRID 1296358 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(O)[CH2:10][N:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:8]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[N:7]1)=[O:5])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[N:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 69416371HCID 69416371, compound

Product 1

HCID 11463589HCID 11463589, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-4-hydroxy-4,5-dihydro-1H-imidazole-4-carboxylic acid ethyl ester I-7b (45 g, 108.8 mmol) and p-toluenesulfonic acid monohydrate (2.1 g, 10.8 mmol) in toluene (540 ml) was heated to reflux overnight. The reaction mixture was cooled and the solvent removed in vacuo. The crude residue was taken up in methylene chloride and washed with water, aqueous sodium bicarbonate, and brine. After drying over anhydrous magnesium sulfate and concentrating, the residue was purified by plug filtration on 600 g silica gel using ethyl acetate/hexanes (20:80) to give pure 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester I-7c (30 g, 69.7%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed in vacuo
  5. washwashed with water, aqueous sodium bicarbonate, and brine
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. concentrationconcentrating
  8. filtrationthe residue was purified by plug filtration on 600 g silica gel

Sources & evidence

ORD record
ord-2b575ecc645d4d21b15443d357452057
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

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