Triethylamine → HCID 12330501, compound

Temperature

0 °C

To a solution of 5-chloro-2-thiophene-carboxylic acid (5.00 g, 30.7 mmol) in 130 mL of acetone is added Et3N (4.29 mL, 30.7 mmol). The mixture is cooled to 0° C. and ethyl chloroformate (3.23 mL, 33.8 mmol) is added. The mixture is stirred at 0° C. for 1 h and sodium azide (3.40 g, 52.3 mmol) is added. The mixture is stirred at 0° C. for 2 h, then poured into 300 mL of ice water and the aqueous layer is extracted with CH2Cl2 (2×). The combined organics are washed with water (2×) and brine, then dried, filtered and concentrated. The crude residue is purified via flash column chromatography eluting with 10% EtOAc/hexanes to provide the title compound (3.00 g, 16.0 mmol) as a white solid. 1H NMR (CDCl3, 300 MHz) δ7.67 (d, 1H), 6.99 (d, 1H).

1. stirringThe mixture is stirred at 0° C. for 2 h
2. extractionthe aqueous layer is extracted with CH2Cl2 (2×)
3. washThe combined organics are washed with water (2×) and brine
4. customdried
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude residue is purified via flash column chromatography
8. washeluting with 10% EtOAc/hexanes

ORD record

ord-8d6cbc0fa3df476697046d44a8eb3267

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612075B2