Water → HCID 14049243, compound

HRID 653411Notes

Reaction equation

HRID 653411 reaction equation
[Br:1][C:2]1[N:3]=[N:4][C:5](Br)=[CH:6][CH:7]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[N:3]=[N:4][C:5]([O:16][C:13]2[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][C:12]=2[N+:17]([O-:19])=[O:18])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 2488523,6-DibromopyridazineHCID 34174194-Amino-2-Nitrophenol

Product 1

HCID 14049243HCID 14049243, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.0 g of 3,6-dibromopyridazine was dissolved in 15 ml of dimethyl sulfoxide. To this solution, a mixture of 2.0 g of 4-amino-2-nitrophenol, 3.6 g of potassium carbonate and 10 ml of water was added and, after flushing with nitrogen, the mixture was reacted at a temperature of from 100° to 110° C. for 2 hours. After the completion of the reaction, the reaction product was cooled and poured into water, and then extracted with methylene chloride. The extract layer was washed with an aqueous sodium hydroxide solution and then with water, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off, whereby 2.4 g of 4-(6-bromo-3-pyridazinyloxy)-3-nitroaniline was obtained. (2) 1.0 g of 4-(6-bromo-3-pyridazinyloxy)-3-nitroaniline obtained in the above step (1) was dissolved in 20 ml of dioxane. To this solution, 8 ml of a dioxane solution containing 0.62 g of 2-nitrobenzoyl isocyanate was added, and the mixture was reacted at room temperature for 15 hours. After the completion of the reaction, the reaction product was poured into water and collected by filtration. The obtained solid was dried and, after the addition of methylene chloride, again subjected to filtration, whereby 1.0 g of the desired product having a melting point of from 222° to 225° C. was obtained.

Workup

  1. additionwas added
  2. customafter flushing with nitrogen
  3. customthe mixture was reacted at a temperature of from 100° to 110° C. for 2 hours
  4. customAfter the completion of the reaction
  5. temperaturethe reaction product was cooled
  6. extractionextracted with methylene chloride
  7. washThe extract layer was washed with an aqueous sodium hydroxide solution
  8. dry with materialwith water, and dried over anhydrous sodium sulfate
  9. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-b10bfde68c80481485f786318d7a0986
Source dataset
uspto-grants-1987_06
Patent number
US04677111

Reaction notes

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