Acetic Acid → HCID 23057961, compound

HRID 346497Notes

Reaction equation

HRID 346497 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.O.C(O)(=O)C.[C:22]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=O)#[N:23]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:27]([C:26]3[CH:25]=[C:24]([CH:32]=[CH:31][CH:30]=3)[C:22]#[N:23])=[N:9][N:8]=2)[N:7]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 8471TriethylamineHCID 1007873-Chloro-6-hydrazinopyridazineHCID 3084833-Cyanobenzoyl chloride

Product 1

HCID 23057961HCID 23057961, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-chloropyridazin-3-yl)hydrazine and triethylamine in THF, 3-cyanobenzoyl chloride was added with cooling in ice, and stirred at room temperature for 1 hour. The reaction solution was combined with water, and the precipitate was collected by filtration, washed with water and diethyl ether to obtain, N′-(6-chloropyridazin-3-yl) -3-cytanobenzohydrazide. To this, acetic acid was added, and the mixture was stirred at 110° C. for 2 hours, the reaction solution was concentrated under reduced pressure, and the resultant crude crystal was washed with ethanol to obtain 3-(6-chloro-1,2,4-triazolo[4,3-b]pyridazin-3-yl)benzonitrile. Dat (F:256).

Workup

  1. temperaturewith cooling in ice
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water and diethyl ether
  4. customto obtain
  5. stirringthe mixture was stirred at 110° C. for 2 hours
  6. concentrationthe reaction solution was concentrated under reduced pressure
  7. washthe resultant crude crystal was washed with ethanol

Sources & evidence

ORD record
ord-1c7bc2b547664a238ea26b716c2e6dbd
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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