Dimethyl Sulfoxide → HCID 21548189, compound

HRID 1604919Notes

Reaction equation

HRID 1604919 reaction equation
[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16](Cl)[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[N:6][CH:5]=1)([O-:3])=[O:2].CS(C)=O.[Cl-].[NH2:25][C:26]([NH2:28])=[NH2+:27].[OH-].[Na+]>O>[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16]([N:25]=[C:26]([NH2:28])[NH2:27])[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[N:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 5460839Carbamimidoylazanium ChlorideHCID 21455925HCID 21455925, compound

Product 1

HCID 21548189HCID 21548189, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3.36 g 3-(5-nitro-1-methyl-2-imidazolyl)-6-chloro-s-triazolo[ 4,3-b] pyridazine were dissolved in 30 ml. dimethyl sulfoxide and mixed at 70°C., while stirring, with 3.4 g guanidinium chloride. 5 ml. water were then added thereto, followed by the dropwise addition of 2.4 ml. 1ON aqueous sodium hydroxide solution, whereafter the reaction mixture was further stirred for an hour at 70°C. After cooling and diluting with water, the precipitated crystals were filtered off with suction, washed with water and dried in a vacuum. 2.5 g of crude product were thus obtained which, after recrystallization from 25 ml. dimethyl formamide, with the addition of active charcoal, gave 1.17 g 3-(5-nitro-1-methyl-2-imidazolyl)-6-(diaminomethylene-amino)-s-triazolo [4,3-b] pyridazine in the form of a yellow material which melted, with decomposition, at 278° - 280°C.

Workup

  1. additionfollowed by the dropwise addition of 2.4 ml
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were filtered off with suction
  4. washwashed with water
  5. customdried in a vacuum
  6. custom2.5 g of crude product were thus obtained which
  7. customafter recrystallization from 25 ml
  8. additiondimethyl formamide, with the addition of active charcoal

Sources & evidence

ORD record
ord-7abf1c64cc994c3f825c931c474fa5e1
Source dataset
uspto-grants-1976_04
Patent number
US03948912

Reaction notes

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