Sodium Carbonate → HCID 178506561, compound

HRID 2359081Notes

Reaction equation

HRID 2359081 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:10]=[CH:9][NH:8][N:7]=1.[I:11]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[I:11][C:10]1[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[N:7][NH:8][CH:9]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 178420845HCID 178420845, compound

Product 1

HCID 178506561HCID 178506561, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-thienyl)-1H-pyrazole (2.9 mmol) was dissolved in 8 mL N,N-dimethylformamide under argon atmosphere. N-Iodosuccinimide (3.1 mmol) was added in small portions. The reaction mixture was stirred at room temperature overnight. 5% aqueous sodium thiosulfate solution and saturated aqueous sodium carbonate solution were added and the mixture was stirred at room temperature for 1 h. The white precipitate was filtered, washed with little cold MTBE and dried in vacuum to afford 540 mg of 4-iodo-3-(2-thienyl)-1H-pyrazole (66% yield). The filtrate was extracted with ethyl acetate. The combined organic layers were successively washed with water and brine, dried over MgSO4, filtered and concentrated to afford 303 mg of 4-iodo-3-(2-thienyl)-1H-pyrazole (34% yield) that was used without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. filtrationThe white precipitate was filtered
  3. washwashed with little cold MTBE
  4. customdried in vacuum

Sources & evidence

ORD record
ord-2a31f391e7ff4df09ed29fcc0d9144c1
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

Loading…