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

HRID 1521666Notes

Reaction equation

HRID 1521666 reaction equation
[Br:1][C:2]1[C:3]([CH:13]2[CH2:15][CH2:14]2)=[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:25])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH:13]2[CH2:15][CH2:14]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[S:25])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 709791496-bromo-5-cyclopropyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 899616266-bromo-5-cyclopropyl-3,4-dihydroquinoline-2(1H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 6-bromo-5-cyclopropyl-3,4-dihydroquinolin-2(1H)-one (147-6; 0.8 g, 0.0030 mol) in toluene (10 mL) was added Lawesson's reagent (1.2 g, 0.003 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): 284.0.

Workup

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

Sources & evidence

ORD record
ord-4b331ed9e3624f218024544b39e0fb64
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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