Potassium Iodide → HCID 18070382, compound

HRID 1259858Notes

Reaction equation

HRID 1259858 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:8][NH:9][C:10]([NH2:12])=S)=[O:7])=[CH:2]1.[OH-].[Na+].BrN1C(C)(C)C(=O)N(Br)C1=O.[I-].[K+].S(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(O)(C)C>[NH2:12][C:10]1[O:7][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[N:8][N:9]=1

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 14798Sodium HydroxideHCID 23665763Sodium BisulfiteHCID 65214101HCID 65214101, compound

Product 1

HCID 18070382HCID 18070382, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An isopropanol (15 mL) solution of 1-(3-furoyl)thiosemicarbazide (1.50 g, 8.10 mmol), a 4 mol/L aqueous sodium hydroxide solution (3.04 mL, 12.2 mmol), and 1,3-dibromo-5,5-dimethylhydantoin (1.74 g, 6.09 mmol) were added to an aqueous (3 mL) solution of potassium iodide (403 mg, 2.43 mmol) under ice cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction solution, a saturated aqueous solution of sodium bisulfite and a saturated aqueous solution of sodium chloride were added. The mixture was subjected to extraction with ethyl acetate and dried over anhydrous sodium sulfate, and then, the solvent was distilled off. The obtained residue was washed with water to obtain the title compound (686 mg, 4.54 mmol) (yield: 56%).

Workup

  1. extractionThe mixture was subjected to extraction with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off
  4. washThe obtained residue was washed with water

Sources & evidence

ORD record
ord-5860669c307b4c1fb75cf588ac694222
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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