Triethylamine → 2-(4-(Ethylsulfonyl)phenyl)acetamide

To a mixture of 2-(4-(ethylsulfonyl)phenyl)acetic acid (3 g, 13.2 mmol), Et3N (4.0 g, 39.6 mmol) and HATU (5.93 g, 15.6 mmol) in anhydrous CH2Cl2 (100 mL) was added NH4Cl (1.54 g, 26.4 mmol). The resulting mixture was stirred at rt overnight. The mixture was diluted with CH2Cl2 (100 mL) and washed with water (3×80 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 50% EtOAc in petroleum ether, gradient to 100%) to afford crude 2-(4-(ethylsulfonyl)phenyl)acetamide. The crude product was added to petroleum ether/ethyl acetate (20 mL, 1/1), then the mixture was stirred for 0.5 h. The mixture was filtered and the filter cake was dried under vacuum to give 2-(4-(ethylsulfonyl)phenyl)acetamide (1.5 g, 50%) as a white solid. LC-MS tR=0.900 min in 0-30AB—2 min chromatography (Welch Xtimate C18, 2.1*30 mm, 3 um), MS (ESI) m/z 269.0 [M+H+CH3CN]+. 1H NMR (DMSO-d6, 400 MHz): δ 7.80 (d, J=8.0 Hz, 2H), 7.58 (broad s, 1H), 7.51 (d, J=8.0 Hz, 2H), 7.00 (broad s, 1H), 3.50 (s, 2H), 3.25 (q, J=7.2 Hz, 2H), 1.08 (t, J=7.2 Hz, 3H).

1. washwashed with water (3×80 mL)
2. dry with materialThe organic layer was dried over anhydrous Na2SO4
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by column chromatography on silica gel (eluting with 50% EtOAc in petroleum ether, gradient to 100%)
6. customto afford crude 2-(4-(ethylsulfonyl)phenyl)acetamide
7. stirringthe mixture was stirred for 0.5 h
8. filtrationThe mixture was filtered
9. customthe filter cake was dried under vacuum

ORD record

ord-ccb0c86df43a4abea7e77bf4fa0adfed

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266886B2