5-(Chlorosulfonyl)-2-ethoxybenzoic acid

Preparation of 5-chlorosulphonyl-2-ethoxy benzoic acid (II) 2-ethoxybenzoic acid (25 g) at 25°C was added to a mixture of thionyl chloride (11 mL), and chlorosulfonic acid (41.3 mL) and the resultant reaction mixture was stirred at RT for 16 h. An off white solid was separated out which is stirred for 1 h. And the reaction mixture was quenched - - with ice (270 g) and water (60 mL). The obtained solid was separated by filtration and solid was washed with water (2xl00mL) and dried under vacuum to afford the title compound as a solid (30 g). 1H NMR (400MHz, CDC1To a stirred solution of 2-(piperazin-l-yl)propane-l-ol (1.0 g, 6.8 mmol) in CH2C12 (11 mL) was added triethylamine (4.6 mL, 34 mmol) at 0C under inert atmosphere. To this, a solution of 5-(chlorosulfonyl)-2-ethoxybenzoic acid (1.8 g, 6.8 mmol) in CH2C12 (11 mL) was added drop wise at 0 C under inert atmosphere. The reaction mixture was allowed to stir at room temperature for 16 h. After completion of reaction (monitored by LCMS analysis), the reaction mixture was directly purified by (without work-up) reverse phase column chromatography (C-18 column, Grace System) by eluting with 0-15% acetonitrile with water to afford the title compound 21 (2.6 g) as an off-white semi solid, which was directly taken for next reaction without further purification. 1H NMR (300 MHz, DMSO-6) delta ppm 7.74 - 7.68 (m, 2 H), 7.26 (d, J = 8.80 Hz, 1 H), 4.17 (q, J = 6.9 Hz, 2 H), 3.36 - 3.34 (m, 3 H), 2.85 - 2.80 (m, 4 H), 2.42 - 2.39 (m, 4 H), 2.32 - 2.29 (m, 2 H), 1.54 - 1.49 (m, 2 H), 1.34 (t, J = 6.9 Hz, 3 H); LCMS (ESI): m/z 373.08 [M+H+]; purity~87%.

Molecular Weight:264.68
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:263.9859223
Monoisotopic Mass:263.9859223
Topological Polar Surface Area:89
Heavy Atom Count:16
Complexity:347
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes