Hydrochloric Acid → 2-Amino-5-(2-pyridylthio)thiazole dihydrochloride

HRID 1656958Notes

Reaction equation

HRID 1656958 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:8][N:9]=1)(=O)C.[ClH:17]>C(O)(=O)C>[ClH:17].[ClH:17].[NH2:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 189547372-Acetylamino-5-(2-pyridylthio)thiazole

Product 1

HCID 189547342-Amino-5-(2-pyridylthio)thiazole dihydrochlorideYield 85.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-acetylamino-5-(2-pyridylthio)thiazole (5.0 g) in a mixture of acetic acid (50 ml) and aqueous 6N-hydrochloric acid (10 ml) was refluxed for 2 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in water. The solution was adjusted to pH 8.5 using aqueous sodium bicarbonate, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The solvent was concentrated under reduced pressure and the residue was triturated with a solution of hydrochloric acid in ethanol. The precipitates were collected by filtration, washed with isopropyl ether and dried in vacuo to give 2-amino-5-(2-pyridylthio)thiazole dihydrochloride (4.60 g, yield: 85.8%). mp: 220°-225° C. (dec.) IR (Nujol ): 2550-2300, 1620, 1595 cm-1

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure
  8. customthe residue was triturated with a solution of hydrochloric acid in ethanol
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with isopropyl ether
  11. customdried in vacuo

Sources & evidence

ORD record
ord-3bd17f0d790f443f8e4ec1e8dfc7376c
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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