Hydrochloric Acid → 2-Amino-5-(4-hydroxyphenylthio)thiazole

HRID 1656980Notes

Reaction equation

HRID 1656980 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:8][N:9]=1)(=O)C.Cl>C(O)C>[NH2:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 157291802-Acetylamino-5-(4-hydroxyphenylthio)thiazole

Product 1

HCID 157291812-Amino-5-(4-hydroxyphenylthio)thiazoleYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetylamino-5-(4-hydroxyphenylthio)thiazole (1.5 g) in a mixture of ethanol (40 ml) and aqueous 6N hydrochloric acid (6 ml) was refluxed for 4.5 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in water. The solution was adjusted to pH 10 using aqueous sodium hydroxide under ice cooling. The precipitates were collected by filtration and recrystallized from a mixture of ethanol and water (3:1) to give 2-amino-5-(4-hydroxyphenylthio)thiazole (1.05 g, yield: 84.0%). mp: 187°-188° C.

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe precipitates were collected by filtration
  5. customrecrystallized from a mixture of ethanol and water (3:1)

Sources & evidence

ORD record
ord-42f8b7f420e045bf8712053badbcde08
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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