p-Toluenesulfonic acid → HCID 22099459, compound

HRID 1457575Notes

Reaction equation

HRID 1457575 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C:9](=[O:24])[NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]=2[OH:23])=[CH:3][CH:2]=1.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37]([OH:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(OCC)(=O)C>[C:31]1([CH3:41])[CH:32]=[CH:33][C:34]([S:37]([OH:40])(=[O:38])=[O:39])=[CH:35][CH:36]=1.[C:31]1([CH3:41])[CH:32]=[CH:33][C:34]([S:37]([OH:40])(=[O:38])=[O:39])=[CH:35][CH:36]=1.[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C:9](=[O:24])[NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]=2[OH:23])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22099429HCID 22099429, compound

Product 1

HCID 22099459HCID 22099459, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl acetate (4 ml) was added to 100 mg of 2-[3-(4-pyridylmethyl)-3-(3-pyridyl)ureido]-4-methoxy-6-tert-butylphenol and the mixture was heated. 94 mg of p-toluenesulfonic acid was added to the above solution. After cooling the solution, the solvent was removed under reduced pressure and the residue was crystallized from an ethanol solution to give 129 mg of 2-[3-(4-pyridylmethyl)-3-(3-pyridyl)ureido]-4-methoxy-6-tert-butylphenol di-p-toluenesulfonate (yield: 70%, melting point: 124°-128 C.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling the solution
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was crystallized from an ethanol solution

Sources & evidence

ORD record
ord-4a938ac5eab04e4e916c9742a5e77c02
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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