Hydrochloric Acid → HCID 15729193, compound

HRID 1656994Notes

Reaction equation

HRID 1656994 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:8][N:9]=1)(=O)C.O1CCCC1.Cl>C(O)C>[NH2:4][C:5]1[S:6][C:7]([S:10][C:11]2[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 15729192HCID 15729192, compound

Product 1

HCID 15729193HCID 15729193, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetylamino-5-(3-hydroxypyridin-2-ylthio)thiazole (2 g) in a mixture of ethanol (40 ml), tetrahydrofuran (20 ml) and aqueous 6N-hydrochloric acid (13 ml) was refluxed for 5 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 extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1). The organic layer was washed with aqueous saturated sodium chloride and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give 2-amino-5-(3-hydroxypyridin-2-ylthio)thiazole (1.15 g, yield: 68.9%). mp: 128°-130° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  5. washThe organic layer was washed with aqueous saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b4932a706a5f4fdeaa46fb3854c5a096
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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