Methane → 3-(5-Nitro-1-methyl-2-imidazolyl)-6-acetamido-s-triazolo[4,3-b]pyridazine

HRID 435589Notes

Reaction equation

HRID 435589 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].[C:20](OC(=O)C)(=[O:22])[CH3:21].C>>[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16]([NH:19][C:20](=[O:22])[CH3:21])[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[N:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 297MethaneHCID 7918Acetic AnhydrideHCID 214559243-(5-Nitro-1-methyl-2-imidazolyl)-6-amino-s-triazolo[4,3-b]pyridazine

Product 1

HCID 214559723-(5-Nitro-1-methyl-2-imidazolyl)-6-acetamido-s-triazolo[4,3-b]pyridazine

Procedure

1.45 g. 3-(5-nitro-1-methyl-2-imidazolyl)-6-amino-s-triazolo[4,3-b]pyridazine was boiled under reflux with 22 ml. acetic anhydride for 1.5 hours at 160° C. bath temperature, the solution obtained was then mixed with charcoal, suction filtered while still hot, washed with a little acetic anhydride and then with ether and dried for 3 hours at 120° C. There was thus obtained 0.79 g. of the desired 3-(5-nitro-1-methyl-2-imidazolyl)-6-acetamido-s-triazolo[4,3-b]pyridazine in the form of yellow-white crystals which melt at 238° - 239° C. and show a change above 230° C.

Workup

  1. temperatureunder reflux with 22 ml
  2. customthe solution obtained
  3. filtrationfiltered while still hot,
  4. washwashed with a little acetic anhydride
  5. dry with materialwith ether and dried for 3 hours at 120° C
  6. custommelt at 238° - 239° C.
  7. customa change above 230° C.

Sources & evidence

ORD record
ord-85cfa5d315674523a3759515d752a771
Source dataset
uspto-grants-1977_02
Patent number
US04006141

Reaction notes

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