Imidazole → HCID 20146342, compound

HRID 569772Notes

Reaction equation

HRID 569772 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.ClCCO[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH2:23][CH2:24][C:25](=[O:28])[NH:26][N:27]=1>CN(C=O)C>[N:7]1([CH2:1][CH2:2][O:4][C:20]2[CH:21]=[CH:16][C:17]([C:22]3[CH2:23][CH2:24][C:25](=[O:28])[NH:26][N:27]=3)=[CH:18][CH:19]=2)[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 20146333HCID 20146333, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20146342HCID 20146342, compoundYield 316.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium-t-butoxide (0.56 g, 0.5 mmol) is added to a solution of imidazole (0.34 g, 0.5 mmol) in dry DMF (10 ml) under N2. The resulting mixture is stirred until homogeneous and then five minutes longer. A solution of 4,5-dihydro-6-(2-chloroethoxyphenyl)-3(2H)-pyridazinone (1.27 g, 0.5 mmol) in dry DMF (20 ml) is added in one portion and the resultant mixture is heated and stirred at 60° for 12 hours. The DMF is then distilled off and the residue taken up in chloroform. The chloroform solution is extracted with 5% aqueous HCl. The aqueous extract is made basic with 10% aqueous sodium carbonate and extracted several times with methylene chloride. The methylene chloride is evaporated, leaving behind 0.45 g of the product 4,5-dihydro-6-[4-(2-(1H-imidazol-1-yl)ethoxyphenyl]-3(2H)-pyridazinone as an amorphous solid.

Workup

  1. stirringstirred at 60° for 12 hours
  2. distillationThe DMF is then distilled off
  3. extractionThe chloroform solution is extracted with 5% aqueous HCl
  4. extractionThe aqueous extract
  5. extractionextracted several times with methylene chloride
  6. customThe methylene chloride is evaporated

Sources & evidence

ORD record
ord-bc7a78321b0f473fba880f23f8a303ce
Source dataset
uspto-grants-1988_03
Patent number
US04734415

Reaction notes

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