Triethylamine → HCID 58366245, compound

2-Thiophenecarboxylic acid hydrazide (200 mg, 1.4 mmol) and Et3N (392 μL, 2.8 mmol) were dissolved in CH2Cl2 (7 mL) and treated with methyl oxalyl chloride (130 μL, 1.4 mmol) dropwise at 0° C. The reaction mixture was warmed slowly to room temperature and stirred for 16 h before the solvent was removed in vacuo. The residue was dissolved in toluene (13 mL) and treated with recrystallized Lawesson's reagent (1.14 g, 2.1 mmol), and warmed at 110° C. for 6 h. Upon completion, the reaction mixture was diluted with EtOAc and washed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. Flash chromatography (SiO2, 3×18 cm, 25% EtOAc-hexanes) afforded the title compound (106 mg, 33%) as a yellow solid: 1H NMR (CDCl3, 500 MHz) δ 7.66 (dd, 1H, J=0.9, 3.7 Hz), 7.58 (dd, 1H, J=0.9, 5.1 Hz), 7.16 (dd, 1H, J=3.9, 4.8 Hz), 4.05 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 166.5, 159.2, 158.4, 131.5, 131.2, 131.17, 128.5, 53.9; HRMS-ESI-TOF m/z 226.9943 ([M+H]+, C8H6N2O2S2 requires 226.9943).

1. customwas removed in vacuo
2. dissolutionThe residue was dissolved in toluene (13 mL)
3. temperaturewarmed at 110° C. for 6 h
4. washwashed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl
5. dry with materialThe organic layer was dried over Na2SO4
6. customthe solvent was removed under reduced pressure

ORD record

ord-d497786323b548468992b6396f3aeeeb

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987312B2