N-Iodosuccinimide → HCID 23449208, compound

HRID 1839331Notes

Reaction equation

HRID 1839331 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][S:10][C:11]1[N:12]=[CH:13][N:14]2[CH:18]=[CH:17][S:16][C:15]=12>ClCCl.[Cl-].[Na+].O>[I:1][C:13]1[N:14]2[C:15]([S:16][CH:17]=[CH:18]2)=[C:11]([S:10][CH3:9])[N:12]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 226315297-Methylthioimidazo[5,1-b]thiazole

Product 1

HCID 23449208HCID 23449208, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-Iodosuccinimide (3.08 g) was added under ice cooling to a solution of 2.28 g of 7-methylthioimidazo[5,1-b]thiazole in dichloromethane. The mixture was stirred at room temperature for 7 hr. Saturated brine was added to the reaction mixture, followed by separation. The organic layer was washed with a dilute aqueous sodium thiosulfate solution and saturated brine in that order, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate:dichloromethane=1:1) to give 3.78 g of 5-iodo-7-methylthioimidazo[5,1-b]thiazole.

Workup

  1. customfollowed by separation
  2. washThe organic layer was washed with a dilute aqueous sodium thiosulfate solution and saturated brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:dichloromethane=1:1)

Sources & evidence

ORD record
ord-1ac3c463b3684cecb09c58d033233cac
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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