Sodium Chloride → HCID 86675401, compound

HRID 407210Notes

Reaction equation

HRID 407210 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl: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+].[Na+].[Cl-]>CC#N.CCOC(C)=O>[NH2:1][C:2]1[C:7]([Cl:18])=[C:6]([Cl:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 86675400HCID 86675400, compound

Product 1

HCID 86675401HCID 86675401, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-amino-6-chloro-3-methoxypicolinate (260 mg, 1.2 mmol) was dissolved in dry CH3CN (7 mL), treated with sulfuryl chloride (120 μL, 1.5 mmol) and stirred for 30 min The solution was stirred with satd aq sodium bicarbonate (NaHCO3; 10 mL) for 20 min and then mixed with EtOAc (20 mL) and satd aq NaCl (10 mL). The aqueous phase was extracted with EtOAc (15 mL), and the combined organic phases were washed with satd aq NaCl (10 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (240 mg, 80%): mp 119-121° C.; 1H NMR (400 MHz, CDCl3) δ 5.04 (s, 2H), 3.97 (s, 3H), 3.93 (s, 3H); EIMS m/z 250.

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (15 mL)
  2. washthe combined organic phases were washed with satd aq NaCl (10 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-8799a37aac7d49f8b903f8ea0140af78
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

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