Phosphorus sulfide (P2S5) → 3-(4,4-Dimethyl-2-thioxo-1,2,3,4,-tetrahydroquinolin-6-yl)benzonitrile

HRID 2300123Notes

Reaction equation

HRID 2300123 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[CH:10]=2)[NH:5][C:4](=O)[CH2:3]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:23]>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[CH:10]=2)[NH:5][C:4](=[S:23])[CH2:3]1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 99653993-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)benzonitrile

Product 1

HCID 99658743-(4,4-Dimethyl-2-thioxo-1,2,3,4,-tetrahydroquinolin-6-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared by heating under reflux overnight a stirred mixture of 3-(4,4-dimethyl-2-oxo-1,2,3,4,-tetrahydroquinolin-6-yl)benzonitrile and an equal weight of phosphorus pentasulfide in pyridine and workup as in the previous example gave a yellow solid: mp 220-223° C. dec. 1H-NMR (DMSO-d6) δ 12.35 (s, 1H), 8.21 (s, 1H), 8.10 (d, 1H, J=6.0 Hz), 7.80 (d, 1H, J=7.9 Hz), 7.72 (s, 1H), 7.65 (m, 2H), 7.21 (d, 1H, J=8.4 Hz), 2.85 (s, 2H), 1.27 (s, 6H); MS (APCI (−)) m/z 291 [M−H]− Anal. Calc. For C18H16N2S 3H2O: C, 62.40, H, 6.40, N, 8.09. Found: C, 62.12, H, 4.88, N 7.77.

Workup

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

Sources & evidence

ORD record
ord-6dcdf597192943e1b4f86b40f9d20d29
Source dataset
uspto-grants-2002_12
Patent number
US06498154B1

Reaction notes

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