Sodium Carbonate → HCID 67260755, compound

HRID 2359094Notes

Reaction equation

HRID 2359094 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:11]=[C:10]([CH3:12])[NH:9][N:8]=2)=[CH:4][CH:3]=1.[I:13]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([I:13])=[C:10]([CH3:12])[NH:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 5260620HCID 5260620, compound

Product 1

HCID 67260755HCID 67260755, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-(5-Chloro-2-thienyl)-5-methyl-1H-pyrazole (40.3 mmol) was dissolved in 70 mL dry N,N-dimethylformamide and cooled to 0° C. under nitrogen atmosphere. N-Iodosuccinimide (42.7 mmol) was added in small portions at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The solution was poured into a mixture of saturated aqueous sodium thiosulfate solution and saturated aqueous sodium carbonate solution (1:1) at room temperature. The precipitate was filtered, washed thoroughly with water, dissolved in ethyl acetate, dried over MgSO4, filtered and evaporated to afford 9.9 g of 3-(5-chloro-2-thienyl)-4-iodo-5-methyl-1H-pyrazole (76% yield) that was used without further purification.

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed thoroughly with water
  4. dissolutiondissolved in ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-38bdeb2159a14d31be15e999213cddf8
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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