Sulfuryl chloride → Methyl 4-amino-6-bromo-5-chloro-3-methoxypicolinate

HRID 378792Notes

Reaction equation

HRID 378792 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14].S(Cl)([Cl:18])(=O)=O.C(=O)(O)[O-].[Na+]>C(#N)C>[NH2:1][C:2]1[C:7]([Cl:18])=[C:6]([Br:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 21696668Methyl 4-amino-6-bromo-3-methoxypicolinate

Product 1

HCID 21696662Methyl 4-amino-6-bromo-5-chloro-3-methoxypicolinate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To methyl 4-amino-6-bromo-3-methoxypyridine-2-carboxylate (1.45 g, 5.56 mmol) in 10 mL of acetonitrile was added sulfuryl chloride, in excess, via pipette until the solution remained yellow. The solution was heated to reflux for 5 min. The reaction mixture was added to saturated sodium bicarbonate and aqueous phase was extracted with diethyl ether (3×). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid. Solid was washed in 10% diethyl ether/petroleum ether and solid filtered to give 0.580 g of a white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 min
  3. extractionwas extracted with diethyl ether (3×)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid
  8. washSolid was washed in 10% diethyl ether/petroleum ether
  9. filtrationsolid filtered

Sources & evidence

ORD record
ord-5e968f9cba0e496a8046e4dab5ba576e
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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