Iodine chloride → HCID 90409363, compound

HRID 516563Notes

Reaction equation

HRID 516563 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Si](C)(C)C)=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:23].[I:24]Cl>ClCCl>[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([I:24])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:23]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 90409195HCID 90409195, compound

Product 1

HCID 90409363HCID 90409363, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To methyl 4-amino-3-chloro-5-methyl-6-(4-(trimethylsilyl)phenyl)picolinate (0.95 g, 2.72 mmol) in dichloromethane (9 mL) was added iodine monochloride (920 mg, 5.67 mmol) in dichloromethane (4.5 mL) dropwise. The reaction was stirred at room temperature for 4 h, then quenched with saturated aqueous sodium thiosulfate, diluted with water, and extracted with dichloromethane (3×). The organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromatography (0-30% ethyl acetate/hexanes) afforded the title compound as a red-orange solid (618 mg, 56%).

Workup

  1. customquenched with saturated aqueous sodium thiosulfate
  2. additiondiluted with water
  3. extractionextracted with dichloromethane (3×)
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (0-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d6c44a30f5a74a70a3dbc6037fdbd9a9
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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