N-Iodosuccinimide → 2-Iodo-4-[(methylsulfonyl)methyl]benzenamine

To a solution of Example 328b (3.80 g, 20.5 mmol) in N,N-dimethylformamide (103 mL) was added N-iodosuccinimide (5.08 g, 22.56 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was quenched with 150 mL 10% aqueous sodium thiosulfate and 100 mL saturated aqueous sodium bicarbonate. The reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride and concentrated. Water was added, and the resulting suspension was stirred at ambient temperature 10 minutes. The suspension was filtered, and the solids collected was rinsed with water, and dried overnight to provide the title compound.

1. customThe reaction mixture was quenched with 150 mL 10% aqueous sodium thiosulfate and 100 mL saturated aqueous sodium bicarbonate
2. extractionThe reaction mixture was extracted with ethyl acetate
3. washThe combined organic layers were washed with saturated aqueous sodium chloride
4. concentrationconcentrated
5. additionWater was added
6. stirringthe resulting suspension was stirred at ambient temperature 10 minutes
7. filtrationThe suspension was filtered
8. customthe solids collected
9. washwas rinsed with water
10. customdried overnight

ORD record

ord-9c9daf4c20ef4ad4829c082efb58cc54

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296741B2