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), washed with 0.33M 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. washwashed with 0.33M citric acid (2×50 ml), brine (50 ml)
4. customdried
5. customevaporated in vacuo
6. customto yield an oil which

ORD record

ord-101bce8bac0e4773a00bb82ec7db40c6

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465728B2