Sodium Thiosulfate → 5-Iodo-2-(methylsulfanyl)imidazo[2,1-b][1,3,4]thiadiazole

HRID 1942318Notes

Reaction equation

HRID 1942318 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]2=[N:8][CH:9]=[CH:10][N:5]2[N:4]=1.C1C(=O)N([I:18])C(=O)C1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC#N>[I:18][C:10]1[N:5]2[C:6]([S:7][C:3]([S:2][CH3:1])=[N:4]2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-Iodosuccinimide2×HCID 582857052-(Methylsulfanyl)imidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 667497445-Iodo-2-(methylsulfanyl)imidazo[2,1-b][1,3,4]thiadiazoleYield 99.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methylsulfanyl-imidazo[2,1-b][1,3,4]thiadiazole (100.00 mg; 0.43 mmol; 1.00 eq.) was dissolved in CH3CN (4.00 ml) protected from light. Then, n-iodosuccinimide (97.22 mg; 0.43 mmol; 1.00 eq.) was added and the reaction was stirred overnight. The reaction was not completed. N-iodosuccinimide (388.88 mg; 1.73 mmol; 4.00 eq.) was added and the reaction was stirred at room temperature. After 1 day, the reaction was finished. A saturated solution of sodium thiosulfate was added and the aqueous phase was extracted 2 times with DCM. The combined organics were washed with saturated aqueous NaHCO3, NH4Cl, brine, dried over MgSO4 to give 127.6 mg of the desired product as a pale yellow solid.

Workup

  1. stirringthe reaction was stirred at room temperature
  2. waitAfter 1 day
  3. extractionthe aqueous phase was extracted 2 times with DCM
  4. washThe combined organics were washed with saturated aqueous NaHCO3, NH4Cl, brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-7a3db6b7a6d54b139206f6c9ead19f94
Source dataset
uspto-grants-2013_03
Patent number
US08389554B2

Reaction notes

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