Sodium Sulfite → HCID 90409928, compound

HRID 516562Notes

Reaction equation

HRID 516562 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Si](C)(C)C)=[C:10]([F:18])[CH:9]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:23].[I:24]Cl.[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([I:24])=[C:10]([F:18])[CH:9]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:23]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 24640Iodine chloride2×HCID 90409458HCID 90409458, compound

Product 1

HCID 90409928HCID 90409928, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 250-mL round bottom flask, equipped with a stir bar, was added methyl 4-amino-3-chloro-6-(3-fluoro-4-(trimethylsilyl)phenyl)picolinate (0.328 g, 0.930 mmol), and dichloromethane (5.0 mL). To this solution iodine monochloride (0.141 mL, 2.79 mmol) was added. The reaction mixture was allowed to stir at room temperature for 18 hrs. Another portion of iodine monochloride (0.141 mL, 2.79 mmol) was added, and the reaction was allowed to stir at room temperature for an additional 4.5 hrs. The reaction mixture was poured into 1 M Na2SO3, and the layers were partitioned. The aqueous phase was extracted with additional ethyl acetate (2×100 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to afford the title compound as a white solid (0.375 g, 99%):

Workup

  1. customTo a 250-mL round bottom flask, equipped with a stir bar
  2. stirringto stir at room temperature for an additional 4.5 hrs
  3. customthe layers were partitioned
  4. extractionThe aqueous phase was extracted with additional ethyl acetate (2×100 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8b338b1521534c59b36654acfdffdd07
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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