Ethanol → 1-Hydroxy-2-(4-acetamido-5-chloro-2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole

HRID 620821Notes

Reaction equation

HRID 620821 reaction equation
[OH:1][N:2]=[C:3]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[C:4]([CH3:6])=O.C(O)C.O.[NH3:17].[C:18]([NH:21][C:22]1[C:29]([Cl:30])=[CH:28][C:25]([CH:26]=O)=[C:24]([O:31][CH3:32])[CH:23]=1)(=[O:20])[CH3:19]>O1CCOCC1>[OH:1][N:2]1[C:3]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:4]([CH3:6])[N:17]=[C:26]1[C:25]1[CH:28]=[C:29]([Cl:30])[C:22]([NH:21][C:18](=[O:20])[CH3:19])=[CH:23][C:24]=1[O:31][CH3:32]

Participants

6

Reactant 4

HCID 702EthanolHCID 12896473Azane;hydrateHCID 212452794-Acetamido-5-chloro-2-methoxybenzaldehydeHCID 737518861-Hydroxyimino-1-(3-pyridyl)acetone

Product 1

HCID 103392791-Hydroxy-2-(4-acetamido-5-chloro-2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1-hydroxyimino-1-(3-pyridyl)acetone (3.3 g) in a mixture of dioxane (80 ml), ethanol (20 ml) and conc. ammonia water (40 ml) was added 4-acetamido-5-chloro-2-methoxybenzaldehyde (4.54 g) and the resultant mixture was stirred at ambient temperature for 3 days. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and 5% hydrochloric acid. The separated aqueous layer was adjusted to pH8.0 with 20% potassium carbonate under stirring and the precipitate was collected by filtration and dried to give 1-hydroxy-2-(4-acetamido-5-chloro-2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (3.1 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and 5% hydrochloric acid
  3. filtrationthe precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-0553c4cd866542008b0948c56fa849ba
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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