Phosphorus sulfide (P2S5) → 6-(3-Fluorophenyl)-4,4-dimethyl-3,4-dihydroquinoline-2(1H)-thione

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Reaction Steps

Prepared by heating under reflux overnight a mixture of 6-(3-fluorophenyl)-4,4-dimethyl-3,4-dihydroquinoline-2(1H)-one and an equal weight of phosphorus pentasulfide was stirred in pyridine. Workup as in the previous example gave a yellow solid, mp 209-211° C. 1H-NMR (DMSO-d6) δ 12.34 (s, 1H), 7.65 (d, 1H J=2.2 Hz) 7.57 (dd, 1H J1=8.24 J2=2.2 Hz), 7.51 (m, 3H), 7.18 (m, 2H), 2.84 (s, 2H), 1.26 (s, 6H). MS m/z 284 [M−H]− Anal. Calc. For C17H16FlNS: C, 71.55, H, 5.65, N, 4.91. Found: C, 71.18, H, 5.59, N, 4.82.

Provenance & Evidence