Sodium Thiosulfate → 2-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

HRID 2409541Notes

Reaction equation

HRID 2409541 reaction equation
C1C(=O)N([I:8])C(=O)C1.[Br:9][C:10]1[S:14][C:13]2=[N:15][CH:16]=[CH:17][N:12]2[N:11]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[Br:9][C:10]1[S:14][C:13]2=[N:15][CH:16]=[C:17]([I:8])[N:12]2[N:11]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 436679232-Bromoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 662215402-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazoleYield 89.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

NIS (3.83 g, 16.2 mmol, 1.1 eq) was added to a solution of 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (3.0 g, 14.7 mmol, 1 eq) in dry DMF (50 mL). The mixture was stirred at RT for 4 h and then poured into aq. Na2S2O3 (10%) and diluted with EtOAc. The organic phase was washed with water, dried and concentrated to give the desired product (pale brown solid; 4.34 g, yield 89%). 1H (300 MHz, CDCl3): δ/ppm 7.29 (1H, s).

Workup

  1. washThe organic phase was washed with water
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-76f3716fc2fd4185841178e892cd0f6b
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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