Water → HCID 21241313, compound

HRID 1761430Notes

Reaction equation

HRID 1761430 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][SH:7])=[O:5].[H-].[Na+].Cl[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[N:18][N:19]=2)[N:16]=1.O>C(O)C>[CH2:2]([O:3][C:4]([CH2:6][S:7][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[N:18][N:19]=2)[N:16]=1)=[O:5])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 3136246-Chloro-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 21241313HCID 21241313, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl thioglycollate, 1.2 g, is dissolved in 30 ml of dry ethanol, to which 400 mg of sodium hydride (60% in an oil) is added under cooling with ice water and the mixture stirred for 10 minutes. Then 1.55 g of 6-chloro-[1,2,4]triazolo[4,3-b]pyridazine is added and stirred at room temperature for 67 hours. The reaction mixture is treated with water and extracted twice with chloroform. The combined extract is washed with saline and dried over anhydrous potassium carbonate. The solvent is evaporated under reduced pressure, and the residue is purified by column chromatogaraphy (on 40 g of silica gel, developed and eluted with ethyl acetate), to give 1.93 g of the desired compound as colorless crystals of m.p. 130°-133° C.

Workup

  1. additionis added
  2. stirringstirred at room temperature for 67 hours
  3. extractionextracted twice with chloroform
  4. extractionThe combined extract
  5. washis washed with saline
  6. dry with materialdried over anhydrous potassium carbonate
  7. customThe solvent is evaporated under reduced pressure
  8. customthe residue is purified by column chromatogaraphy (on 40 g of silica gel, developed and eluted with ethyl acetate)

Sources & evidence

ORD record
ord-a0dea2d497e9488395e82ea059d378de
Source dataset
uspto-grants-1989_05
Patent number
US04826834

Reaction notes

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