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

HRID 1656976Notes

Reaction equation

HRID 1656976 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-hydroxymethyl-5-(4-pyridylthio)thiazole dihydrochloride (2.5 g, yield: 75.3%). mp: 231°-237° C. (dec.) IR (Nujol) 3350, 2300, 1610, 1560 cm-1

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-469a87eb89334295ba12d827506f33e1
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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