N-Iodosuccinimide → 7-Iodo-5-methylimidazo[5,1-b]thiazole

5-Methylimidazo[5,1-b]thiazole (6.90 g) was dissolved in 500 ml of dichloromethane. N-Iodosuccinimide (10.6 g) was added to the solution. The mixture was stirred at room temperature for 24 hr. N-Iodosuccinimide (1.06 g) was added thereto, followed by stirring for additional one hr. The reaction solution was washed with an aqueous sodium thiosulfate solution and brine in that order, dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under the reduced pressure. The residue was dissolved in 200 ml of dichloromethane and 100 ml of ethyl acetate. Silica gel (30 g) was added to the solution. The mixture was stirred. The silica gel was removed by filtration. The filtrate was washed with 200 ml of a mixed solution of dichloromethane:ethyl acetate=2:1. The filtrate was concentrated under the reduced pressure to give 13.08 g of 7-iodo-5-methylimidazo[5,1-b]thiazole.

1. stirringby stirring for additional one hr
2. washThe reaction solution was washed with an aqueous sodium thiosulfate solution and brine in that order
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. customThe solvent was removed by distillation under the reduced pressure
6. dissolutionThe residue was dissolved in 200 ml of dichloromethane
7. additionSilica gel (30 g) was added to the solution
8. stirringThe mixture was stirred
9. customThe silica gel was removed by filtration
10. washThe filtrate was washed with 200 ml of a mixed solution of dichloromethane
11. concentrationThe filtrate was concentrated under the reduced pressure

ORD record

ord-315b0da8c41540409d20e1cdece1616c

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458780B1