Lawesson's reagent → HCID 178425914, compound

HRID 570981Notes

Reaction equation

HRID 570981 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]#[C:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1COCC1>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:7])=[S:32])=[CH:4][C:3]=1[C:11]#[C:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 70557832HCID 70557832, compound

Product 1

HCID 178425914HCID 178425914, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methyl-3-[(quinolin-3-yl)ethynyl]benzoic acid (0.3 g, 1.3 mmol) and Lawesson's reagent (0.5 ml, 1.3 mmol) in THF (10 ml) was stirred at ambient temperature for 1 hr under an atmosphere of nitrogen. The reaction mixture was concentrated and the crude product was purified by flash chromatography on silica gel (elution with 10% ethyl acetate in n-hexane) to provide 4-methyl-3-[(quinolin-3-yl)ethynyl]thiobenzoic acid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by flash chromatography on silica gel (elution with 10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-4bf1055917984adcb5f73eaf99bc63a8
Source dataset
uspto-grants-2015_05
Patent number
US09024021B2

Reaction notes

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