Lawesson's reagent → 6-Bromo-3,4-dihydroquinoline-2(1H)-thione

HRID 1521578Notes

Reaction equation

HRID 1521578 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH2:6][CH2:5]2.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:22]2)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[S:22])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 573709906-Bromo-3,4-dihydroquinoline-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

6-bromo-3,4-dihydroquinolin-2-(1H)-one (1.00 g, 4.42 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane2,4-disulfide (0.895 g, 2.21 mmol) were suspended in toluene (110 mL) and then heated to 110° C. overnight. The reaction was then cooled to room temperature and concentrated under reduced pressure. Dichloromethane was added, giving a mixture that was filtered to provide the title compound: LCMS m/z 243.95 [M+2+H]+; 1H NMR (500 MHz, DMSO) δ 7.44 (s, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H), 2.92-2.89 (m, 2H), 2.81-2.78 (m, 2H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionDichloromethane was added
  4. customgiving a mixture that
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-36f8bb2f68874059bec83322927d43bc
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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