Potassium Carbonate → HCID 15729190, compound

HRID 1656991Notes

Reaction equation

HRID 1656991 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7](Br)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[SH:11][C:12]1[NH:13][CH:14]=[CH:15][N:16]=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[NH:13][CH:14]=[CH:15][N:16]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3502602-Acetamido-5-bromo-1,3-thiazoleHCID 178527877HCID 178527877, compound

Product 1

HCID 15729190HCID 15729190, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-acetylamino-5-bromothiazole (1.9 g), 2-mercaptoimidazole (0.9 g) and potassium carbonate (1.5 g) in N,N-dimethylformamide (30 ml) was heated at 90° C. for 2.5 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was extracted with methanol. 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 fraction containing the objective compound were combined and concentrated under reduced pressure to give 2-acetylamino-5-(2-imidazolylthio)thiazole (1.8 g, yield: 87.4%). mp: 230°-235° C. (dec.) IR (Nujol): 3150, 3100, 1710, 1550, 1290 cm-1

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with methanol
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customto give solid
  5. washeluted with a mixture of chloroform and methanol (10:1)
  6. additionThe fraction containing the objective compound
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-875d8fa812fa4104ab2986c44d585cc8
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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