Potassium Carbonate → HCID 15729192, compound

HRID 2380632Notes

Reaction equation

HRID 2380632 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7](Br)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[OH:11][C:12]1[C:13]([SH:18])=[N:14][CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:18][C:13]2[C:12]([OH:11])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3502602-Acetamido-5-bromo-1,3-thiazoleHCID 178516238HCID 178516238, compound

Product 1

HCID 15729192HCID 15729192, compoundYield 110.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-acetylamino-5-bromothiazole (1.8 g), 3-hydroxy-2-mercaptopyridine (1.3 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (40 ml) was heated at 90° C. for 3.5 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. 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-(3-hydroxypyridin-2-ylthio) thiazole (2.4 g, yield: 89.9%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with water
  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-ea2696cc81d4492c861fb26a9c5227d0
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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