Triethylamine → HCID 14100224, compound

HRID 648426Notes

Reaction equation

HRID 648426 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].ClC([O:13][C:14](Cl)(Cl)Cl)=O.[NH2:18][C:19]1[CH:24]=[CH:23][N:22]=[N:21][CH:20]=1.C(N(CC)CC)C>O1CCOCC1>[N:22]1[CH:23]=[CH:24][C:19]([NH:18][C:14]([NH:5][C:4]2[CH:3]=[C:2]([F:1])[CH:8]=[C:7]([F:9])[CH:6]=2)=[O:13])=[CH:20][N:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 965953,5-DifluoroanilineHCID 2984924-Aminopyridazine

Product 1

HCID 14100224HCID 14100224, compoundYield 126.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2.7 grams (0.021 mole) of 3,5-difluoroaniline in 100 ml of dioxane was added via syringe 1.5 ml (0.013 mole ) of trichloromethyl chloroformate. The reaction mixture was heated under reflux for 18 hours, cooled to ambient temperature, and 2.0 grams (0.021 mole) of 4-aminopyridazine and 7.01 ml (0.05 mole) of triethylamine were added. The reaction mixture was heated at 50° C. for one day, cooled to ambient temperature and filtered. The filter cake was washed with dioxane and dried. The solid was slurried in hot water for one hour. The mixture was filtered and the filter cake dried to give 4.1 grams of N-(4-pyridazinyl)-N'-(3,5-difluorophenyl)urea; m.p. 272°-273° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperatureThe reaction mixture was heated at 50° C. for one day
  4. temperaturecooled to ambient temperature
  5. filtrationfiltered
  6. washThe filter cake was washed with dioxane
  7. customdried
  8. filtrationThe mixture was filtered
  9. customthe filter cake dried

Sources & evidence

ORD record
ord-940f93c7d696426e99a62738d5f6e0b3
Source dataset
uspto-grants-1988_04
Patent number
US04735650

Reaction notes

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