Dimethylformamide → 3-(1-METHYL-5-NITRO-2-IMIDAZOLYL)-6-FORMYLAMINO-S-TRIAZOLO [4,3-b]PYRIDAZINE

HRID 1729864Notes

Reaction equation

HRID 1729864 reaction equation
[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16]([NH2:19])[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[N:6][CH:5]=1)([O-:3])=[O:2].CN(C)[CH:22]=[O:23].C(OC(=O)C)(=O)C>C(O)=O>[CH3:9][N:8]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][N:6]=[C:7]1[C:10]1[N:14]2[N:15]=[C:16]([NH:19][CH:22]=[O:23])[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 214559243-(5-Nitro-1-methyl-2-imidazolyl)-6-amino-s-triazolo[4,3-b]pyridazine

Product 1

HCID 214560043-(1-METHYL-5-NITRO-2-IMIDAZOLYL)-6-FORMYLAMINO-S-TRIAZOLO [4,3-b]PYRIDAZINE

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

100 mg. 3-(5-nitro-1-methyl-2-imidazolyl)-6-amino-s-triazolo [4,3-b]pyridazine were suspended in 1.3 ml. dimethyl formamide and, after the addition of 1.5 ml. of the mixed anhydride obtainable from formic acid and acetic anhydride, stirred at ambient temperature until no more starting material could be detected by thin layer chromatography. The almost clear solution thus obtained was, after filtration, evaporated in a vacuum and the residue brought to crystallization with ether. There were thus obtained 72 mg. (65 percent of theory) 3-(1-methyl-5-nitro-2-imidazolyl)-6-formylamino-s-triazolo[4,3-b]pyridazine in the form of yellowish crystals which melt, with decomposition, at 200° - 204° C.

Workup

  1. customThe almost clear solution thus obtained
  2. filtrationafter filtration
  3. customevaporated in a vacuum
  4. customthe residue brought to crystallization with ether
  5. customat 200° - 204° C.

Sources & evidence

ORD record
ord-695898540b1347618a12eb1d229d7f9c
Source dataset
uspto-grants-1976_11
Patent number
US03989832

Reaction notes

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