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

HRID 435588
Notes
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Reaction equation

HRID 435588 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=O.P(Cl)(Cl)(Cl)=O.[N+:14]([C:17]1[N:21]([CH3:22])[C:20]([C:23]2[N:27]3[N:28]=[C:29]([NH2:32])[CH:30]=[CH:31][C:26]3=[N:25][N:24]=2)=[N:19][CH:18]=1)([O-:16])=[O:15]>O1CCOCC1>[N+:14]([C:17]1[N:21]([CH3:22])[C:20]([C:23]2[N:27]3[N:28]=[C:29]([N:32]=[CH:1][N:3]4[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]4)[CH:30]=[CH:31][C:26]3=[N:25][N:24]=2)=[N:19][CH:18]=1)([O-:16])=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 174291-PiperidinecarboxaldehydeHCID 24813Phosphorus oxychlorideHCID 214559243-(5-Nitro-1-methyl-2-imidazolyl)-6-amino-s-triazolo[4,3-b]pyridazine

Product 1

HCID 214559653-(5-Nitro-1-methyl-2-imidazolyl)-6-(1-piperidinyl-methyleneamino)-s-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 312751,4-Dioxane
Solvent

Procedure

2.85 ml. N-formyl-piperidine in 10 ml. dioxan were stirred with 2.4 ml. phosphorus oxychloride, which was introduced portionwise at 35° - 40° C., for 30 minutes at this temperature, then 1.5 g. crude 3-(5-nitro-1-methyl-2-imidazolyl)-6-amino-s-triazolo[4,3-b]pyridazine was added and the reaction mixture was stirred for 1.5 hours at 35° - 40° C. The solution obtained was now poured into 75 ml. ice water, filtered with suction and the clear filtrate was rendered alkaline (about pH 10) with concentrated aqueous ammonia, cooled, left to stand for some time and the resultant crystals (1.28 g.) filtered off with suction and recrystallized from 25 ml. isopropanol, with the addition of charcoal, 0.82 g. of the desired 3-(5-nitro-1-methyl-2 -imidazolyl)-6-(1-piperidinyl-methyleneamino)-s-triazolo[4,3-b]pyridazine thereby being obtained in the form of yellowish-white crystals which melt at 187° - 189° C.

Workup

  1. customThe solution obtained
  2. additionwas now poured into 75 ml
  3. filtrationice water, filtered with suction
  4. temperaturecooled
  5. waitleft
  6. filtrationthe resultant crystals (1.28 g.) filtered off with suction
  7. customrecrystallized from 25 ml
  8. additionisopropanol, with the addition of charcoal, 0.82 g

Sources & evidence

ORD record
ord-14606b33e553424cab368e0488fbce06
Source dataset
uspto-grants-1977_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04006141

Reaction notes

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