Acetonitrile → HCID 86703140, compound

HRID 2204340Notes

Reaction equation

HRID 2204340 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.S([O:16][CH3:17])(OC)(=O)=O.CC#N.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]([CH3:4])[C:17](=[O:16])[CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 467387064-Bromo-2-chloro-5-methoxypyridine

Product 1

HCID 86703140HCID 86703140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-2-chloro-5-methoxypyridine [1020253-15-9] (1 g, 4.5 mmol) in dimethyl sulfate (1.9 mL, 19.5 mmol) was stirred at 120° C. for 16 h in a sealed tube. After cooling to rt, CH3CN and a saturated aqueous NaHCO3 solution were added and the mixture was stirred at rt over the weekend. CH2Cl2 was added and the phases were separated. The organic layer was dried (Na2SO4), filtered and concentrated to give the title compound as a white powder. ESI-MS: tR=0.57 min; [M+H]+ 218/220 (LC-MS 1).

Workup

  1. customthe phases were separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-79572fbb1f974f1b9cb763aac7064f17
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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