Lawesson's reagent → HCID 59426224, compound

HRID 506017Notes

Reaction equation

HRID 506017 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]([NH2:16])=O)=[CH:4]1)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14](=[S:26])[NH2:16])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59426170HCID 59426170, compound

Product 1

HCID 59426224HCID 59426224, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Ethyl-6-methoxy-1H-indole-3-carboxamide (120 mg, 0.55 mmol), Lawesson's reagent (240 mg, 0.6 mmol), and toluene (2 mL) are heated at 90° C. for 90 min. The reaction mixture is concentrated and purified by silica gel chromatography (EtOAc/CH2Cl2, 1/9) to yield 1-ethyl-6-methoxy-1H-indole-3-thiocarboxamide as a yellow solid (92 mg, 71%).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompurified by silica gel chromatography (EtOAc/CH2Cl2, 1/9)

Sources & evidence

ORD record
ord-7024314168ba472c990d6568c276fb8a
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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