Water → Ethyl 2-methanesulfonamidobenzoate

Temperature

5 °C

To a cooled, stirred solution of 2-amino-benzoic acid ethyl ester (10.0 g, 60.5 mmol) in ether (50 mL) at 5° C. was added triethylamine (8.44 mL, 60.5 mmol). methanesulfonyl chloride (4.68 mL, 60.5 mmol) in ethyl acetate (50 mL) was added dropwise to the mixture, was stirred for 1 hour at 5° C. then at room temperature for 18 hours. Water (100 mL) was added to the stirring mixture and was extracted with ethyl acetate (3×50 mL). The combined organic was washed with water (2×50 mL) and saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate, filtered and evaporated. The residue was stirred with warm methanol (30 mL) for 30 minutes and cooled to room temperature. The crystalline material was filtered and rinsed with a minimum of methanol. 2-Methanesulfonylamino-benzoic acid ethyl ester was isolated as a white solid (7.0 g, 48%). 1H NMR (400 MHz, CDCl3, δ, ppm): 10.52 (br s, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.74 (d, J=8.5 Hz, 1H), 7.56 (t, J=7.8 Hz, 1H), 7.13 (t, J=7.7 Hz, 1H), 4.40 (q, J=7.0 Hz, 2H), 3.06 (s, 3H), 1.42 (t, J=7.0 Hz, 3H). MS=266 (M+Na)+.

1. waitat room temperature for 18 hours
2. extractionwas extracted with ethyl acetate (3×50 mL)
3. washThe combined organic was washed with water (2×50 mL) and saturated aqueous sodium chloride
4. dry with materialThe organic layer was dried over magnesium sulfate
5. filtrationfiltered
6. customevaporated
7. stirringThe residue was stirred with warm methanol (30 mL) for 30 minutes
8. temperaturecooled to room temperature
9. filtrationThe crystalline material was filtered
10. washrinsed with a minimum of methanol

ORD record

ord-24626f933d6b4020bc92ba51ecb4efb1

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633173B2