Potassium Carbonate → Isoflavone

HRID 1905059Notes

Reaction equation

HRID 1905059 reaction equation
SC1SCCN=1.O[C:8]1[CH:28]=[CH:27][C:11]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][C:17](O)=[CH:18][C:19]=3O)[O:14][C:13]=2CBr)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[C:12]([C:11]2[CH:27]=[CH:28][CH:8]=[CH:9][CH:10]=2)=[CH:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 155987314',5,7-Trihydroxy-2-bromomethylisoflavoneHCID 178527880HCID 178527880, compound

Product 1

HCID 72304Isoflavone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Mercaptothiazoline (35 mg) was added to a mixture of 4',5,7-trihydroxy-2-bromomethylisoflavone (50 mg), anhydrous potassium carbonate (21 mg) and N,N-dimethylformamide (1 ml), and the resulting mixture was stirred at room temperature for 10 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform), giving 32 mg of 4',5,7-trihydroxy-2-[2-thiazolin-2-ylthio)-methyl]isoflavone as amorphous powder.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-e9c760604e144cb3a0fe50b6500b7c7f
Source dataset
uspto-grants-1989_06
Patent number
US04841077

Reaction notes

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