Hydrochloric Acid → 2-Amino-5-(5-trifluoromethylpyridin-2-ylthio)thiazole

HRID 1657001Notes

Reaction equation

HRID 1657001 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[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[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=2)=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 15729199HCID 15729199, compound

Product 1

HCID 157292002-Amino-5-(5-trifluoromethylpyridin-2-ylthio)thiazoleYield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetylamino-5-(5-trifluoromethylpyridin-2-ylthio)thiazole (3.2 g) in a mixture of ethanol (60 ml), tetrahydrofuran (30 ml) and aqueous 6N-hydrochloric acid (10 ml) was refluxed for 3 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 mixture of tetrahydrofuran and ethyl acetate (1:1) 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: 150 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 to give 2-amino-5-(5-trifluoromethylpyridin-2-ylthio)thiazole (2.1 g, yield: 75.8%). mp: 135°-138° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with mixture of tetrahydrofuran and ethyl acetate (1:1)
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customto give solid
  8. washeluted with a mixture of chloroform and methanol (10:1)
  9. additionThe fractions containing the objective compound
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1a5db51116744fc969e6708d504580b
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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