Hydrochloric Acid → 2-Amino-5-(2-methyl-1,3,4-thiadiazol-5-ylthio)thiazole

HRID 1656984Notes

Reaction equation

HRID 1656984 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[S:15][C:14]([CH3:16])=[N: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[S:15][C:14]([CH3:16])=[N:13][N:12]=2)=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 157291832-Acetylamino-5-(2-methyl-1,3,4-thiadiazol-5-ylthio)thiazole

Product 1

HCID 157291842-Amino-5-(2-methyl-1,3,4-thiadiazol-5-ylthio)thiazoleYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetylamino-5-(2-methyl-1,3,4-thiadiazol-5-ylthio)thiazole (3.3 g) in a mixture of ethanol (70 ml), tetrahydrofuran (50 ml) and aqueous 6N-hydrochloric acid (200 ml) was refluxed for 6.5 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 aqueous sodium bicarbonate and extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1). The organic layer was washed with aqueous saturated sodium chloride and dried over magnesium sulfate. The organic 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-(2-methyl-1,3,4-thiadiazol-5-ylthio)thiazole (0.85 g, Yield: 58.2%). mp: 203°-205° C. (dec.)

Workup

  1. temperaturewas refluxed for 6.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  5. washThe organic layer was washed with aqueous saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe organic solvent was concentrated under reduced pressure
  8. customto give solid
  9. washeluted with a mixture of chloroform and methanol (10:1)
  10. additionThe fractions containing the objective compound
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2239689ff594d578d37a16de12d9a63
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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