Hydrochloric Acid → HCID 15729191, compound

HRID 2380631Notes

Reaction equation

HRID 2380631 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[NH:12][CH:13]=[CH:14][N:15]=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[NH:15][CH:14]=[CH:13][N:12]=2)=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15729190HCID 15729190, compound

Product 1

HCID 15729191HCID 15729191, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetylamino-5-(2-imidazolylthio)thiazole (1.8 g) in a mixture of concentrated hydrochloric acid (10 ml) and ethanol (50 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 sodium bicarbonate with cooling. The precipitates were collected by filtration, washed with water and dried in vacuo to give 2-amino-5-(2-imidazolylthio)thiazole (0.35 g). The filtrate was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1), washed with aqueous saturated sodium chloride and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 100 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure give 2-amino-5-(2-imidazolylthio)thiazole (0.55 g). Total amount of 2-amino-5-(2-imidazolylthio)thiazole was 0.90 (yield: 60.4%).

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. temperaturewith cooling
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-4e5ee25dc83a42bd9ed3ea24f939a115
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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