Sodium Hydroxide → HCID 178522566, compound

HRID 1595400Notes

Reaction equation

HRID 1595400 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[N:14][C:13]=2[C:27]([NH:29][C:30]2[S:31][CH:32]=[CH:33][N:34]=2)=[O:28])=[CH:8][CH:7]=1)(=O)C.[OH-].[Na+]>CC(C)=O>[OH:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[NH:16][C:15]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[N:14][C:13]=2[C:27]([NH:29][C:30]2[S:31][CH:32]=[CH:33][N:34]=2)=[O:28])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178475834HCID 178475834, compound

Product 1

HCID 178522566HCID 178522566, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-(4-Acetoxymethylphenyl)-2-(1-naphthyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (2.98 g) obtained in Example 60(2) was dissolved in acetone (250 ml) and 0.25 M aqueous sodium hydroxide solution (56 ml) was added under ice-cooling. The mixture was stirred at room temperature for 2 hr. Acetone was evaporated under reduced pressure and the residue was acidified with aqueous citric acid solution and extracted with ethyl acetate. The ethyl acetate layer was washed with water and the solvent was evaporated. The obtained residue was recrystallized from ethyl acetate to give 5-(4-hydroxymethylphenyl)-2-(1-naphthyl)-N-(2-thiazolyl)imidazole-4-carboxamide (2.08 g), melting point 226-228° C.

Workup

  1. temperaturecooling
  2. customAcetone was evaporated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. customthe solvent was evaporated
  6. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-02414eb8142248c4876849da06f04d20
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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