Dimethyl Disulfide → HCID 23159742, compound

HRID 1011434Notes

Reaction equation

HRID 1011434 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][CH:6]=2.[CH3:14][S:15]SC>C1COCC1>[CH3:13][O:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([S:15][CH3:14])[CH:3]=[N:4]2

Participants

4

Reactant 2

HCID 12232Dimethyl DisulfideHCID 231597643-Bromo-5-methoxyquinoline

Product 1

HCID 23159742HCID 23159742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-bromo-5-methoxy quinoline (2.37 g, 10 mmol) prepared in stage B of example 10 in THF (25 mL) was added 2.5M n-buLi (4 mL, 10 mmol) at −78° C. The solution is stirred at −78° C. for 45 min and dimethyl disulfide (1.8 g, 20 mmol) is added. The resultant solution is stirred for 3 hours and then quenched with saturated NH4Cl (30 mL). Extraction with dichloromethane, drying, filtering and evaporation in vacuo afford the title compound

Workup

  1. customquenched with saturated NH4Cl (30 mL)
  2. extractionExtraction with dichloromethane
  3. customdrying
  4. filtrationfiltering
  5. customevaporation in vacuo

Sources & evidence

ORD record
ord-602bdd1194b34418b09bb0bb9e75ce08
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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