Phosphorus sulfide (P2S5) → HCID 9922428, compound

HRID 2120752Notes

Reaction equation

HRID 2120752 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) 8 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 C17H16CINS: 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-bde40e033dea48c68ce69dae82ee8775
Source dataset
uspto-grants-2004_02
Patent number
US06693103B2

Reaction notes

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