Trimethylsilyl iodide → HCID 178428623, compound

HRID 37115Notes

Reaction equation

HRID 37115 reaction equation
C[O:2][C:3]1[C:8]([C:9]([N:11]2[C:16]3[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:15]=3[O:14][C:13]([CH3:25])([CH3:24])[CH2:12]2)=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1.C[Si](I)(C)C>C(Cl)(Cl)(Cl)Cl.O>[OH:2][C:3]1[C:8]([C:9]([N:11]2[C:16]3[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:15]=3[O:14][C:13]([CH3:25])([CH3:24])[CH2:12]2)=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 19934607HCID 19934607, compound

Product 1

HCID 178428623HCID 178428623, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

In 6 ml of carbon tetrachloride was dissolved 0.4 g of 3,4-dihydro-4-[(2-methoxypyridin-3-yl)carbonyl]-2,2-dimethyl-6-nitro-2H-1,4-benzoxazine followed by dropwise addition of 0.26 g of trimethylsilyl iodide. The mixture was heated at 50° C. for 2 hours and, then, cooled. The reaction mixture was diluted with water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered, the filtrate was concentrated under reduced pressure, and methanol was added to the concentrate for crystallization., Recrystallization from ethyl acetate gave 0.31 g of 3,4-dihydro-4-[(2-hydroxypyridin-3-yl)carbonyl]-2,2-dimethyl-6-nitro-2H-1,4-benzoxazine.

Workup

  1. temperaturecooled
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure, and methanol
  6. additionwas added to the
  7. concentrationconcentrate for crystallization
  8. custom, Recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-11c08331de734e57b5b07e97e4aae238
Source dataset
uspto-grants-1995_05
Patent number
US05420126

Reaction notes

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