Tripropylamine → 3,6-Dimethylimidazo[2,1-b]thiazole-5-sulfonamide

HRID 2051128Notes

Reaction equation

HRID 2051128 reaction equation
[CH3:1][C:2]1[N:3]2[C:9]([S:10](O)(=[O:12])=[O:11])=[C:8]([CH3:14])[N:7]=[C:4]2[S:5][CH:6]=1.C([N:18](CCC)CCC)CC>O(Cl)Cl>[CH3:1][C:2]1[N:3]2[C:9]([S:10]([NH2:18])(=[O:12])=[O:11])=[C:8]([CH3:14])[N:7]=[C:4]2[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 7616TripropylamineHCID 144224683,6-Dimethylimidazo [2,1-b]thiazole-5-sulfonic acid

Product 1

HCID 144224783,6-Dimethylimidazo[2,1-b]thiazole-5-sulfonamideYield 53.8%

Reagents, catalysts & solvents 1

HCID 24646Chlorine monoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 2.8 g of 3,6-dimethylimidazo [2,1-b]thiazole-5-sulfonic acid in 3.4 ml of phophorus oxychloride, 1.8 g of tri-n-propylamine is added under cooling and stirred for 30 minutes at 60° C. The reaction solution after cooling is poured into ice water and extracted with dichloromethane. The dichloromethane layer is collected, dried and then distilled to remove dichloromethane. The residue is dissolved in 35 ml of acetonitrile, to which 3.8 ml of aqueous ammonia is added under cooling and stirred for 30 minutes at room temperature. The acetonitrile is distilled off under reduced pressure, and to the residue is added water. The precipitated crystalline solid is collected by filtration and washed with tetrachloromethane to give 1.5 g of the title compound as colorless crystals. mp. 177°-178° C.

Workup

  1. additionis added
  2. temperatureunder cooling
  3. temperatureThe reaction solution after cooling
  4. extractionextracted with dichloromethane
  5. customThe dichloromethane layer is collected
  6. customdried
  7. distillationdistilled
  8. customto remove dichloromethane
  9. dissolutionThe residue is dissolved in 35 ml of acetonitrile, to which 3.8 ml of aqueous ammonia
  10. additionis added
  11. temperatureunder cooling
  12. stirringstirred for 30 minutes at room temperature
  13. distillationThe acetonitrile is distilled off under reduced pressure
  14. additionto the residue is added water
  15. filtrationThe precipitated crystalline solid is collected by filtration
  16. washwashed with tetrachloromethane

Sources & evidence

ORD record
ord-a748cac5bf1b4fa8a3498226cbc0f1f5
Source dataset
uspto-grants-1991_05
Patent number
US05017212

Reaction notes

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