Potassium Carbonate → 2-Acetylamino-5-(2-methyl-1,3,4-thiadiazol-5-ylthio)thiazole

HRID 1656983Notes

Reaction equation

HRID 1656983 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7](Cl)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[SH:11][C:12]1[S:16][C:15]([CH3:17])=[N:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:11][C:12]2[S:16][C:15]([CH3:17])=[N:14][N:13]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 46841342-Acetamido-5-chlorothiazoleHCID 178434161HCID 178434161, compound

Product 1

HCID 157291832-Acetylamino-5-(2-methyl-1,3,4-thiadiazol-5-ylthio)thiazoleYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-acetylamino-5-chlorothiazole (1.76 g), 5-mercapto-2-methyl-1,3,4-thiadiazole (1.3 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (40 ml) was heated at 120° C. for 4 hours with stirring. The reaction mixture was concentrated under reduced pressure and water was added to this residue. The mixture 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: 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-acetylamino-5-(2-methyl-1,3,4-thiadiazol-5-ylthio)thiazole (1.65 g, yield: 60.7%). mp: 242°-244° C. IR (Nujol): 3250, 1695, 1550, 1300 cm-1

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to this residue
  3. extractionThe mixture was extracted with a mixture of tetrahydrofuran and ethyl acetate (1:1)
  4. washwashed with aqueous saturated sodium chloride
  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-33375a0fb4514007ba34e570f50669df
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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