Captamine → 2-[(Imidazo[1,2-b]pyridazin-6-yl)sulfanyl]-N,N-dimethylethan-1-amine

HRID 1607307Notes

Reaction equation

HRID 1607307 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][SH:5].C[O-].[Na+].Cl[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[N:16]=1>CO>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][S:5][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[N:16]=1

Participants

5

Reactant 3

HCID 25799CaptamineHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-HCID 10942334Sodium Methoxide

Product 1

HCID 200765592-[(Imidazo[1,2-b]pyridazin-6-yl)sulfanyl]-N,N-dimethylethan-1-amineYield 57.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
150 °C

Procedure

To 20 ml of methanol is dissolved 2.8 g of 2-dimethylaminoethanethiol. To this, 20 ml of 2M solution of sodium methoxide in methanol and 3 g of 6-chloroimidazo[1,2-b]pyridazine are added successively and the mixture is heated in a sealed tube for 4 hours at 150° C. After cooling, the solvent is evaporated and the residue is treated with water. The mixture is then extracted with methylene chloride. The organic layer is separated, washed with saturated aqueous solution of sodium chloride and dried over MgSO4. Evaporation of the solvent gives 2.5 g of the title compound as pale yellow crystals.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated
  3. additionthe residue is treated with water
  4. extractionThe mixture is then extracted with methylene chloride
  5. customThe organic layer is separated
  6. washwashed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b0a18372df534c32a0fc95a851856073
Source dataset
uspto-grants-1989_09
Patent number
US04864022

Reaction notes

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