1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde → HCID 21455952, compound

HRID 435596Notes

Reaction equation

HRID 435596 reaction equation
[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([CH:10]=O)=[N:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH:13]([C:15]1[N:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[NH2:14]>>[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:16]3[N:17]=[CH:18][CH:19]=[CH:20][C:15]3=[N:13][N:14]=2)=[N:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 214559923-Hydrazinylpyridazine hydrochloride

Product 1

HCID 21455952HCID 21455952, compound

Procedure

4 g. lead tetraacetate were suspended in 40 ml. glacial acetic acid, 1.5 g. of the hydrazone obtained from 1.55 g. 5-nitro-1-methyl-imidazole-2-aldehyde and 1.1 g. 3-hydrazinopyridazine hydrochloride (prepared by heating for 30 minutes in 20 ml. 50% aqueous methanol at 50° C. and subsequent neutralization with sodium acetate) were added, while stirring at 50° - 60° C., the reaction mixture further stirred for 15 minutes, considerably evaporated in a vacuum, the resultant crystals filtered off with suction, triturated with water and dried for 2 hours in a vacuum at 120° C., 1.05 g. of the desired 3-(5-nitro-1-methyl-2 -imidazolyl)-s-triazolo[4,3-b]pyridazine being obtained, which has a melting point of 235° - 237° C.

Workup

  1. stirringthe reaction mixture further stirred for 15 minutes
  2. customconsiderably evaporated in a vacuum
  3. filtrationthe resultant crystals filtered off with suction
  4. customtriturated with water
  5. customdried for 2 hours in a vacuum at 120° C.

Sources & evidence

ORD record
ord-87c4e649def04683be3dc4e4f579bb0a
Source dataset
uspto-grants-1977_02
Patent number
US04006141

Reaction notes

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