Sodium Hydroxide → HCID 14623680, compound

HRID 1199964Notes

Reaction equation

HRID 1199964 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]([CH3:21])[CH2:19][C:18](=[O:22])[NH:17][N:16]=2)=[CH:11][CH:10]=1.[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[Na+].[OH-].[Na+]>O>[CH3:21][C:20]1[C:15]([C:12]2[CH:11]=[CH:10][C:9]([C:3]3[C:2]([CH3:1])=[CH:7][C:6](=[O:8])[NH:5][N:4]=3)=[CH:14][CH:13]=2)=[N:16][NH:17][C:18](=[O:22])[CH:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 19864465HCID 19864465, compound

Product 1

HCID 14623680HCID 14623680, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,4-bis(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)benzene (1.41 g), sodium m-nitrobenzenesulphonate (2.20 g) and sodium hydroxide (1 g) in water (100 ml) was stirred under reflux until a clear solution was obtained. Stirring under reflux was continued for one hour and the reaction mixture was cooled to room temperature and filtered. The filtrate was acidified with acetic acid to give a white precipitate, which could not be collected by filtration as it passed through the sinter funnel. The mixture was basified with sodium hydroxide to pH 14 and the resulting solution was then taken to pH 10 with aqueous sodium bicarbonate and allowed to stand at room temperature for 16 hours. A pale yellow solid was collected and was dissolved in dilute aqueous sodium hydroxide. The solution was taken to pH 11 with saturated aqueous ammonium chloride to afford 1,4-bis(4-methyl-6-oxo-1,6-dihydropyridazin-3-yl)benzene (1.02 g), m.p.>250° C.

Workup

  1. temperatureunder reflux until a clear solution
  2. customwas obtained
  3. stirringStirring
  4. temperatureunder reflux
  5. filtrationfiltered
  6. customto give a white precipitate, which could not
  7. filtrationbe collected by filtration as it
  8. waitto stand at room temperature for 16 hours
  9. customA pale yellow solid was collected
  10. dissolutionwas dissolved in dilute aqueous sodium hydroxide

Sources & evidence

ORD record
ord-432321ab3ae04c4190899d5c0042f951
Source dataset
uspto-grants-1990_02
Patent number
US04904664

Reaction notes

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