Triethylamine → 2,6-Dichloro-3-(propylsulfonamido)benzoic acid

Temperature

0 °C

3-Amino-2,6-dichlorobenzoic acid (1.40 g, 6.82 mmol) was dissolved in dry dichloromethane (66.7 mL). Triethylamine (4.09 mL, 29.4 mmol) was added, and the mixture was chilled to 0° C. Propane-1-sulfonyl chloride (2.48 mL, 22 mmol) was then added via syringe. Once the addition was complete, the mixture was allowed to warm to ambient temperature and stir for 1 hour. The mixture was concentrated in vacuo and diluted with diethyl ether. The mixture was washed with 0.25M NaOH (80 mL), and the aqueous layer was acidified to a pH of 1 using 1.0M HCl. The aqueous layer was extracted with 15% 2-propanol:DCM (2×300 mL). The organic layer was collected, dried over sodium sulfate, and concentrated to afford 2,6-dichloro-3-(propylsulfonamido)benzoic acid (1.55 g, 4.96 mmol, 74.4% yield). 1H NMR (400 MHz, d6-DMSO) δ 9.77-9.75 (s, 1H), 7.84-7.80 (d, 1H), 7.71-7.68 (d, 1H), 3.82-3.72 (m, 2H), 1.89-1.70 (m, 2H), 1.05-1.03 (m, 3H).

1. additionOnce the addition
2. temperatureto warm to ambient temperature
3. concentrationThe mixture was concentrated in vacuo
4. additiondiluted with diethyl ether
5. washThe mixture was washed with 0.25M NaOH (80 mL)
6. extractionThe aqueous layer was extracted with 15% 2-propanol
7. customThe organic layer was collected
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated

ORD record

ord-37456d3944554efbbaa8d7dbca395a02

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08338452B2