Iodine → 1-[5-(2,4-Dichlorophenyl)sulfanyl-4-iodo-2-thienyl]ethanone

Temperature

60 °C

To a dark solution of I2 (0.958 g 7.5 mmol) in acetonitrile (20 mL), was added t-butyl nitrite (0.4 g, 3.75 mmol) slowly. The resulting solution was heated to 60° C. for 20 min. To the above solution, was added dropwise of a solution of 1-[4-amino-5-(2,4-dichlorophenyl)sulfanyl-2-thienyl]ethanone (0.8 g, 2.5 mmol) in acetonitrile (20 mL). The resulting mixture was heated at 60° C. for 2 hours. After this time the reaction mixture was quenched with sodium hydroxide aqueous solution (1 M), and extracted with ethyl acetate. The organic layer was separated, dried (Na2SO4) and concentrated. The crude solid was purified by silica gel chromatography using a 98:2 mixture of hexane and ethyl acetate as eluent to afford the title product as a yellow solid (1.07 g, 46.2% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.16 (1H, s), 7.82 (1H, dd), 7.47 (1H, dd), 7.05 (1H, dd), 2.54 (3H, s). MS m/z: 428.7 [M+H]+.

1. temperatureThe resulting mixture was heated at 60° C. for 2 hours
2. customAfter this time the reaction mixture was quenched with sodium hydroxide aqueous solution (1 M)
3. extractionextracted with ethyl acetate
4. customThe organic layer was separated
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe crude solid was purified by silica gel chromatography
8. additiona 98:2 mixture of hexane and ethyl acetate as eluent

ORD record

ord-7b3ce851b219410e821679a491fb8c73

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680139B2