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HETEROCYCLES, Vol. 80, No. 1, 2010
19
145.6, 133.7, 129.6 (2C), 128.8 (2C), 117.8 (dq, J = 40.3, 273.1 Hz), 107.9-107.8 (m), 21.6. F NMR
–73.75 (d, J = 9.8, 3F), –118.28 (dq, J = 31.4, 9.8 Hz, 1F). HRMS(EI): calcd for C11H8OF4; 232.0511.
Found; 232.0514.
Celecoxib
To 1f (a mixture of the stereoisomers was used, 114 mg, 0.49 mmol) in a 4:1 mixture of DMF and H2O (5
mL) was added 4-hydrazinobenzenesulfonamide hydrochloride (133 mg, 0.60 mmol) and the mixture was
stirred at 40 °C for 12 h. After cooling to rt, H2O (40 mL) was added to the mixture. The mixture was
extracted with Et2O (40 mL x 3), and the organic layer was washed with H2O (40 mL x 3), and brine (40
mL). The organic layer was dried over MgSO4, concentrated under reduced pressure. Purification by
column chromatography (silica gel/hexane-Et2O) gave Celecoxib (150 mg) in 80% yield; a white crystal;
mp 154–156 °C (lit.,8a 157–159 °C): IR (KBr): 3267, 1164 cm-1. 1H NMR 7.91 (d, J = 8.4 Hz, 2H), 7.48
(d, J = 8.4 Hz, 2H), 7.18 (d, J = 8.4 Hz, 2H), 7.11 (d, J = 8.0 Hz, 2H), 6.75 (s, 1H), 4.85 (s, 2H), 2.39 (s,
13
3H). C NMR 145.2, 144.1 (q, J = 38.7 Hz), 142.5, 141.2, 139.8, 129.7 (2C), 128.7 (2C), 127.5 (2C),
125.6, 125.5 (2C), 121.0 (q, J = 269.0 Hz), 106.3 (q, J = 1.9 Hz), 21.3. 19F NMR –63.03 (s, 3F).
ACKNOWLEDGEMENTS
We are grateful to Mitsubishi Gas Chemical Company Inc. for their donation of DFMBA.
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