Phosphorus sulfide (P2S5) → HCID 9922428, compound

HRID 2300122Notes

Reaction equation

HRID 2300122 reaction equation
[Cl: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>[Cl: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 9965656HCID 9965656, compound

Product 1

HCID 9922428HCID 9922428, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared by heating under reflux overnight a mixture of 6-(3-chlorophenyl)-4,4-dimethyl-3,4-dihydroquinoline-2(1H)-one and an equal weight of phosphorus pentasulfide in pyridine was stirred. Removal of the pyridine in vacuo followed by treating the residue with 6N hydrochloric acid and recrystallization of the residue in ethanol gave the product as a yellow solid: mp. 197-1980° C. 1H-NMR (DMSO-d6) δ 12.34 (s, 1H), 7.75 (m, 1H), 7.64 (m, 2H), 7.57 (dd, 1H J=9.3 and 2.1 Hz), 7.48 (t, 1H, J=7.7 Hz), 7.41 (m, 1H), 7.20 (d, 1H, J=8.3 Hz), 3.34 (s, 2H), 1.26 (s,6H); MS (APCI (−)) m/z 300 [M−H]− Anal. Calc. For C17H16ClNS: C, 67.65, H, 5.34, N, 4.64. Found: C, 67.77, H, 5.57, N 4.54.

Workup

  1. customPrepared
  2. temperatureby heating
  3. temperatureunder reflux overnight
  4. customRemoval of the pyridine in vacuo
  5. additionby treating the residue
  6. customwith 6N hydrochloric acid and recrystallization of the residue in ethanol

Sources & evidence

ORD record
ord-5a5457a7f7764a34befe5b43a60e5ea2
Source dataset
uspto-grants-2002_12
Patent number
US06498154B1

Reaction notes

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