Acetic Acid → HCID 21886036, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium thiomethoxide (1.87 g, 26.8 mmol) in EtOH (26.8 mL, anhydrous) was added to a suspension of 4-(3-bromo-benzenesulfonyl)-5-nitro-thiophene-2-carbonitrile (10 g, 26.8 mmol, Example 286: step e) in THF (67 mL, anhydrous) portionwise at −78° C. The temperature of the reaction was maintained at −78° C. with stirring for 1 hour. The reaction was quenched with acetic acid (2 mL, 34.9 mmol) at −78° C. followed by warming the reaction mixture to rt and then filtered. The yellow solids were washed with diethyl ether and saved. The filtrate was concentrated in vacuo resulting in a residue that was suspended in diethyl ether and stirred at rt overnight. The solids were filtered from the suspension. The combined yellow solids were dried under high vacuum to afford the title compound (8.77 g, 87.4%). 1H-NMR (DMSO-d6): δ 8.45 (s, 1H), 7.97–8.16 (m, 3H), 7.62–7.67 (m, 1H), 2.71 (s, 3H).

Provenance & Evidence