Imidazole → N-{3-[(2-oxo-1,2-dihydroquinolin-6-yl)oxy]propyl}-1H-imidazole-1-carboxamide

HRID 1856745Notes

Reaction equation

HRID 1856745 reaction equation
[CH:1]1N=C[N:3]([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])[CH:2]=1.N1C=CN=C1.NCC[CH2:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[CH:27]=[CH:26]2>CS(C)=O>[N:8]1([C:6]([NH:3][CH2:2][CH2:1][CH2:21][O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[NH:29][C:28](=[O:33])[CH:27]=[CH:26]3)=[O:7])[CH:9]=[CH:10][N:11]=[CH:12]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 100136326-(3-Aminopropoxy)carbostyril

Product 1

HCID 15479723N-{3-[(2-oxo-1,2-dihydroquinolin-6-yl)oxy]propyl}-1H-imidazole-1-carboxamideYield 60.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N,N-carbonyldiimidazole (139 g) and imidazole (117 g) in dimethylsulfoxide (2 liters) is added with stirring 6-(3-aminopropoxy)carbostyril (200 g) in portions under ice-cooling. The mixture is further stirred at room temperature for one day, and poured into ice-water. The precipitated crystals are collected by filtration, and washed with water. The crystals thus obtained are further washed successively with ethanol and diethyl ether, and dried to give 6-[3-(1-imidazolyl)carbonylaminopropoxy]carbostyril (162 g) as a white powder.

Workup

  1. temperaturecooling
  2. filtrationThe precipitated crystals are collected by filtration
  3. washwashed with water
  4. customThe crystals thus obtained
  5. washare further washed successively with ethanol and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-b77e024e57d94b1e9015a2e424b0f4eb
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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