Methylamine → HCID 21455934, compound

HRID 1729870Notes

Reaction equation

HRID 1729870 reaction equation
[N+:1]([C:4]1[N:8]([CH2:9]COC(=O)C)[C:7]([C:15]2[N:19]3[N:20]=[C:21](Cl)[CH:22]=[CH:23][C:18]3=[N:17][N:16]=2)=[N:6][CH:5]=1)([O-:3])=[O:2].CN.[N+](C1N(CCOC(=O)C)C(C2N3N=[C:47]([NH:50][CH3:51])[CH:48]=[CH:49][C:44]3=NN=2)=NC=1)([O-])=O>O1CCOCC1>[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:15]2[N:19]3[N:20]=[C:21]([N:50]4[CH2:47][CH2:48][CH2:49][CH2:44][CH2:51]4)[CH:22]=[CH:23][C:18]3=[N:17][N:16]=2)=[N:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 21455910HCID 21455910, compoundHCID 21455917HCID 21455917, compound

Product 1

HCID 21455934HCID 21455934, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.42 g. crude 3-(5-nitro-1-β-acetoxyethyl-2-imidazolyl)-6-chloro-s-triazolo[4,3-b]pyridazine (see Example 14 for the preparation thereof) was dissolved in 3 ml. dioxan, mixed with 0.36 ml. 33 percent aqueous methylamine solution, maintained at 60° C. for half an hour, then evaporated in a vacuum at a bath temperature of 50° C. The residue was dissolved in 2 ml. isopropanol, left to stand for about one hour at ambient temperature and the precipitated crystals then filtered off with suction, washed with isopropanol and ether and recrystallized (0.1 g.) from about 5 ml. isopropanol, with the addition of charcoal, to give 0.054 g. of the desired 3-(5-nitro-1-β-acetoxyethyl-2-imidazolyl)-6-methylamino-s-triazolo-[4,3-b]pyridazine, which has a melting point of 221° - 233° C.

Workup

  1. customfor the preparation
  2. dissolution) was dissolved in 3 ml
  3. customevaporated in a vacuum at a bath temperature of 50° C
  4. dissolutionThe residue was dissolved in 2 ml
  5. waitisopropanol, left
  6. filtrationthe precipitated crystals then filtered off with suction
  7. washwashed with isopropanol and ether
  8. customrecrystallized (0.1 g.) from about 5 ml
  9. additionisopropanol, with the addition of charcoal
  10. customto give 0.054 g

Sources & evidence

ORD record
ord-c25213de3da645499339835f08cd7ffc
Source dataset
uspto-grants-1976_11
Patent number
US03989832

Reaction notes

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