Sodium Carbonate → HCID 67260872, compound

HRID 2359102Notes

Reaction equation

HRID 2359102 reaction equation
CN1C(CCC)=CC(C2SC=CC=2C)=N1.[CH3:16][N:17]1[C:21]([C:22]2[S:23][CH:24]=[CH:25][C:26]=2[CH3:27])=[CH:20][C:19]([CH2:28][CH2:29][CH3:30])=[N:18]1.[I:31]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+].IC1C(C2SC=CC=2C)=NN(C)C=1CCC>CN(C)C=O>[I:31][C:20]1[C:19]([CH2:28][CH2:29][CH3:30])=[N:18][N:17]([CH3:16])[C:21]=1[C:22]1[S:23][CH:24]=[CH:25][C:26]=1[CH3:27]

Participants

8

Reactant 6

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 67260246HCID 67260246, compoundHCID 67260377HCID 67260377, compoundHCID 67260830HCID 67260830, compound

Product 1

HCID 67260872HCID 67260872, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-methyl-3-(3-methyl-2-thienyl)-5-propyl-1H-pyrazole and 1-methyl-5-(3-methyl-2-thienyl)-3-propyl-1H-pyrazole (85:15, 3.7 mmol) in 10 mL dry N,N-dimethylformamide under argon atmosphere was added N-iodosuccinimide (4.6 mmol) 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, then extracted with MTBE. The combined organic extracts were successively washed with water and brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (toluene:ethyl acetate 100:0 to 0:100) to afford 928 mg of a mixture of 4-iodo-1-methyl-3-(3-methyl-2-thienyl)-5-propyl-1H-pyrazole and 4-iodo-1-methyl-5-(3-methyl-2-thienyl)-3-propyl-1H-pyrazole (85:15; 61% yield) that was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. extractionextracted with MTBE
  3. washThe combined organic extracts were successively washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (toluene:ethyl acetate 100:0 to 0:100)

Sources & evidence

ORD record
ord-4aac2cd76a70455ea099a51dd3fb7b41
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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