Lawesson's reagent → 6-bromo-5-fluoro-3,4-dihydroquinoline-2(1H)-thione

HRID 1521659Notes

Reaction equation

HRID 1521659 reaction equation
[Br:1][C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH2:6][CH2:5]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[S:23])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 709801486-Bromo-5-fluoro-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 899616816-bromo-5-fluoro-3,4-dihydroquinoline-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 6-bromo-5-fluoro-3,4-dihydroquinolin-2(1H)-one (146-5; 0.45 g, 0.00184 mol) in toluene (10 mL) was added Lawesson's reagent (0.745 g, 1.00184 mol). Reaction mass heated at 120° C. and maintained for 2 h. The reaction mixture was cooled, quenched with sodium bicarbonate solution and extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the title compound. 1H NMR (400 MHz, DMSO) δ 12.364 (s, 1H), 7.543-7.503 (t, J=8.0 Hz, 1H), 6.895-6.874 (d, J=0.1-8.4 Hz, 1H) 2.968-2.930 (t, J=7.2 Hz, 2H), 2.843-2.805 J 8.0 Hz, 2H): MS (M 1): 260.1.

Workup

  1. customReaction mass
  2. temperaturemaintained for 2 h
  3. temperatureThe reaction mixture was cooled
  4. customquenched with sodium bicarbonate solution
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-12cb7119cc26412a9227f06bf5acf95b
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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