Hydrochloric Acid → 2-Amino-4-hydroxymethyl-5-(4-pyridylthio)thiazole dihydrochloride

HRID 2380616Notes

Reaction equation

HRID 2380616 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:8]([CH2:10][OH:11])[N:9]=1)(=O)C.[ClH:19]>C(O)C>[ClH:19].[ClH:19].[NH2:4][C:5]1[S:6][C:7]([S:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:8]([CH2:10][OH:11])[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 157291752-Acetylamino-4-hydroxymethyl-5-(4-pyridylthio)thiazole

Product 1

HCID 197868072-Amino-4-hydroxymethyl-5-(4-pyridylthio)thiazole dihydrochlorideYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetylamino-4-hydroxymethyl-5-(4-pyridylthio)thiazole (3.0 g) in a mixture of concentrated hydrochloric acid (8 ml) and ethanol (100 ml) was refluxed for 2.5 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with acetone. The precipitates were collected by filtration, washed with isopropyl ether and were recrystallized from a mixture of ethanol and isopropyl ether to give 2-amino-4-hydroxymethy-5-(4-pyridylthio)thiazole dihydrochloride (2.5 g, yield: 75.3%).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was triturated with acetone
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with isopropyl ether
  6. customwere recrystallized from a mixture of ethanol and isopropyl ether

Sources & evidence

ORD record
ord-9b791e09c7fe43b0be61d43d745723c7
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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