Sodium Iodide → HCID 15239969, compound

HRID 1653634Notes

Reaction equation

HRID 1653634 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[N+:14]([O-])[C:13]=2[C:19]([O:21][CH3:22])=[O:20])[N:4]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+].[CH3:34][N:35]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)C(Cl)=O>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[C:13]([C:19]([O:21][CH3:22])=[O:20])=[N:14][C:15]([N:35]([CH3:34])[CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:16][CH:17]=2)[N:4]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 10464985N-benzyl-N-methylcarbamoyl chlorideHCID 14425903methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate N-oxide

Product 1

HCID 15239969HCID 15239969, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

20 g (77.1 mmol) of methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate N-oxide, 15 g (116 mmol) of diisopropylethylamine and 46.2 g (308.2 mmol) of sodium iodide were suspended in 200 ml of acetonitrile and stirred at room temperature for 15 minutes. To this mixture, 21.2 g (115.4 mmol) of N-methyl-N-benzylcarbamoyl chloride dissolved in 20 ml of acetonitrile was added at room temperature. The mixture was refluxed. Foaming started at a temperature slightly lower than the boiling point, and such foaming terminated in about 30 minutes. The reaction was continued for further 10 minutes. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water, dried, concentrated and then purified by silica gel column chromatography to obtain the desired product.

Workup

  1. additionwas added at room temperature
  2. temperatureThe mixture was refluxed
  3. customsuch foaming terminated in about 30 minutes
  4. waitThe reaction was continued for further 10 minutes
  5. additionThe reaction solution was poured into water
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated
  10. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-cf59d4b1fa2d4d4481b66b5822abfd7e
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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