Hydrochloric Acid → HCID 22631480, compound

HRID 1840434Notes

Reaction equation

HRID 1840434 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][S:7][C:8]1[N:9]=[CH:10][N:11]2[CH:15]=[CH:14][S:13][C:12]=12)=[N+]=[N-].Cl.[H][H]>C1COCC1.C(O)C.O.[Pd]>[NH2:1][CH2:4][CH2:5][CH2:6][S:7][C:8]1[N:9]=[CH:10][N:11]2[CH:15]=[CH:14][S:13][C:12]=12

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 22631922HCID 22631922, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22631480HCID 22631480, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

7-(3-Azidopropyl)thioimidazo[5,1-b]thiazole (1.46 g) was dissolved in 30 ml of THF ethanol and 6 ml of water, and 6.1 ml of a 1 N aqueous hydrochloric acid solution and 1.46 g of 10% Pd-C were added to the solution. The air in the reaction vessel was replaced by hydrogen, and the contents of the reaction vessel were stirred at room temperature for 24 hr. The catalyst was removed by filtration on Celite, and was washed with water. The filtrate was concentrated under the reduced pressure. A 1 N aqueous sodium hydroxide solution (20 ml) was added to the residue, and the mixture was extracted with dichloromethane five times. The extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation to prepare 1.15 g of 7-(3-aminopropyl)thioimidazo[5,1-b]thiazole.

Workup

  1. customThe catalyst was removed by filtration on Celite
  2. washwas washed with water
  3. concentrationThe filtrate was concentrated under the reduced pressure
  4. additionA 1 N aqueous sodium hydroxide solution (20 ml) was added to the residue
  5. extractionthe mixture was extracted with dichloromethane five times
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation
  8. customto prepare 1.15 g of 7-(3-aminopropyl)thioimidazo[5,1-b]thiazole

Sources & evidence

ORD record
ord-7ab91ee2e1cd441e83bcba9f88e7a2c9
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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