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

HRID 277878Notes

Reaction equation

HRID 277878 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=O)[CH2:12][C:11]3([CH3:20])[CH3:19])[CH:5]=[CH:6][CH:7]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[S:22])[CH2:12][C:11]3([CH3:20])[CH3:19])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 99433246-(3-fluorophenyl)-4,4-dimethyl-3,4-dihydroquinoline-2(1H)-one

Product 1

HCID 98355256-(3-Fluorophenyl)-4,4-dimethyl-3,4-dihydroquinoline-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  1. customPrepared
  2. temperatureby heating
  3. temperatureunder reflux overnight

Sources & evidence

ORD record
ord-6fd03746b2af4d839c50ee6f2e42ee4d
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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