Hydrochloric Acid → N'-(6-chloropyridazin-3-yl)-3-dimethylaminobenzohydrazide

HRID 346498Notes

Reaction equation

HRID 346498 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:21])[C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](O)=[O:16].Cl.C1COCC1>O>[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH:9][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][CH:20]=[C:12]([N:11]([CH3:10])[CH3:21])[CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 668373-(Dimethylamino)benzoic acidHCID 1007873-Chloro-6-hydrazinopyridazine

Product 1

HCID 23057966N'-(6-chloropyridazin-3-yl)-3-dimethylaminobenzohydrazide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (6-chloropyridazin-3-yl)hydrazine, 3-dimethylaminobenzoic acid, WSCD hydrochloride and THF was stirred at room temperature for 2 hours. The reaction solution was combined with water, and the precipitate was collected by filtration, washed with water and isopropyl ether to obtain N′-(6-chloropyridazin-3-yl)-3-dimethylaminobenzohydrazide. To this, ethylene glycol was added and the mixture was stirred at 160° C. for 4 hours. After allowing to cool to room temperature, followed by purification by a standard method, 6-chloro-3-(3-dimethylaminophenyl)-1,2,4-triazolo[4,3-b]pyridazine was obtained. Dat (F:274).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water and isopropyl ether

Sources & evidence

ORD record
ord-f96b58283a464c0391a3952f47847d79
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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