4-Iodobenzenesulfonyl chloride → N-(2-ethoxyethyl)-4-iodobenzenesulphonamide

2-Ethoxyethylamine (2.14 g, 24 mmol) and diisopropylethylamine (4.2 ml, 24 mmol) were dissolved in DCM (50 ml) and cooled to 0° C. To this was added pipsyl chloride (6.05 g, 20 mmol) in portions and the reaction stirred for 18 hours. Volatiles were evaporated in vacuo. The residue was dissolved in EtOAc (50 ml), extracted 1N citric acid (2×50 ml), brine (50 ml), dried and evaporated in vacuo to yield an oil which solidified on standing to give the title compound as a pale yellow solid (6.97 g, 98%). NMR: 1.01 (t, 3H), 2.89 (q, 2H), 3.30 (m, 4H), 7.53 (d, 2H), 7.75 (t, 1H), 7.97 (d, 2H); m/z 354 (M−H)−.

1. customVolatiles were evaporated in vacuo
2. dissolutionThe residue was dissolved in EtOAc (50 ml)
3. extractionextracted 1N citric acid (2×50 ml), brine (50 ml)
4. customdried
5. customevaporated in vacuo
6. customto yield an oil which

ORD record

ord-f00c15a7580a4694a24b293c5acc3408

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07442697B2