Lawesson's reagent → 6-Bromo-2-thioxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

HRID 1521652Notes

Reaction equation

HRID 1521652 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=O)[CH2:6][CH2:5][C:4]=2[C:3]=1[C:13]#[N:14].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[S:24])[CH2:6][CH2:5][C:4]=2[C:3]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 709774556-Bromo-2-oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

Product 1

HCID 891560546-Bromo-2-thioxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile (145-2; 1.3 g, 0.0052 mol) in toluene (20 mL) was added Lawesson's reagent (2.1 g, 0.0052 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. 1H NMR (400 MHz, CDCl3) δ 1H NMR (400 MHz, DMSO-d6) δ 7.612-7.561 (m, 1H), 6.980-6.959 (t, J=8.4 Hz, 1H), 3.779-3.769 (d, J=4 Hz, 4H).

Workup

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

Sources & evidence

ORD record
ord-6c33252167a24270b9f9a223af999235
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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