N-Iodosuccinimide → (5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-(4-methoxyphenyl)amine

HRID 1043665Notes

Reaction equation

HRID 1043665 reaction equation
[S:1]1[C:5]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[N:4][N:3]2[CH:15]=[CH:16][N:17]=[C:2]12.[I:18]N1C(=O)CCC1=O>CN(C)C=O>[I:18][C:15]1[N:3]2[C:2]([S:1][C:5]([NH:6][C:7]3[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=3)=[N:4]2)=[N:17][CH:16]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 67334626Imidazo[2,1-b][1,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine

Product 1

HCID 67333843(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-(4-methoxyphenyl)amineYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazo[2,1-b][1,3,4]thiadiazol-2-yl-(4-methoxyphenyl)amine (0.455 g, 1.85 mmol) was dissolved in N,N-dimethylformamide (8 mL) and N-iodosuccinimide (2.03 mmol, 0.48 g) was added in one portion. The reaction mixture was stirred at room temperature for 22 hours in the absence of light. Solvent was evaporated and the residue was purified by column chromatography (Biotage™/Flash, silica, ethylacetate:dichloromethane 2:8 to 0:10) to give 0.11 g of (5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-(4-methoxyphenyl)amine as an off-white solid (16% yield).

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by column chromatography (Biotage™/Flash, silica, ethylacetate:dichloromethane 2:8 to 0:10)

Sources & evidence

ORD record
ord-2df6e5595321443987d5cd8da28b36d5
Source dataset
uspto-grants-2013_10
Patent number
US08563550B2

Reaction notes

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