Lawesson's reagent → 6-bromo-7-fluoro-3,4-dihydroquinoline-2(1H)-thione

HRID 1521639Notes

Reaction equation

HRID 1521639 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[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[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[NH:8][C:7](=[S:23])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 434576896-bromo-7-fluoro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 891560686-bromo-7-fluoro-3,4-dihydroquinoline-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 6-bromo-7-fluoro-3,4-dihydroquinolin-2(1H)-one (122-3; 13 g, 0.02 mol) in toluene (50 mL) was added Lawesson's reagent (21.54 g, 0.0532 mol). Reaction mass was refluxed at 100° C. for 12 h. The reaction mixture was concentrated and directly purified by silica gel column chromatography to obtain title compound. MS (M+1): 261.88.

Workup

  1. customReaction mass
  2. concentrationThe reaction mixture was concentrated
  3. customdirectly purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3d12549ee2264474ae15997a598247d9
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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