Potassium ethanethioate → HCID 11206726, compound

HRID 1825297Notes

Reaction equation

HRID 1825297 reaction equation
[C:1]([S:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:3])[CH3:2].Cl.ClCC1C=NC2C(C=1)=CC=CC=2.C([O-])(=S)C.[K+]>CC(C)=O>[C:1]([S:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86597577HCID 86597577, compound

Product 1

HCID 11206726HCID 11206726, compoundYield 160.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Acetylthiomethylquinoline—3-Chloromethylquinoline hydrochloride (5.2 g) was taken up in acetone (100 ml) followed by the addition of potassium thioacetate (1.8 g) and allowed to stir at rt overnight. The reaction mixture was absorbed onto silica gel and chromatographed (silica gel, step gradient 0–50% ether/petroleum ether) to give the title compound as an orange solid (4.2 g). 1H NMR δ(DMSO-d6): 8.85 (1H, d, J=2 Hz), 8.25(1H, d, J=2 Hz), 8.01(1H, d, J=8.4 Hz), 7.95 (1H, d, J=8.4 Hz), 7.74 (1H, t, J=8.4 Hz), 7.61 (1H, t, J=8.4 Hz), 4.33 (2H, s), 2.38 (3H, s).

Workup

  1. customThe reaction mixture was absorbed onto silica gel
  2. customchromatographed (silica gel, step gradient 0–50% ether/petroleum ether)

Sources & evidence

ORD record
ord-d631f860b43143aeb51a744971bf08be
Source dataset
uspto-grants-2006_05
Patent number
US07045626B2

Reaction notes

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